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Tootsie (1982)
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Tootsie (1982)

Michael Dorsey is an unemployed actor with an impossible reputation. In order to find work and fund his friend's play he dresses as a woman, Dorothy Michaels, and lands the part in a daytime drama. Dorsey loses himself in this woman role and essentially becomes Dorothy Michaels, captivating women al β€¦l around the city and inspiring them to break free from the control of men and become more like Dorsey's initial identity. This newfound role, however, lands Dorsey in a hot spot between a female friend/'lover,' a female co-star he falls in love with, that co-star's father who falls in love with him, and a male co-star who yearns for his affection. (Read More)

Subgenre:
cult film
Themes:
unemploymentbreak upcelebrityseductiondrinkinglovefriendship
Mood:
slow burn
Locations:
farmnightclubrestaurantbarnew york city
Characters:
crying babycheating on one's girlfriendlow self esteemsingle motheractresslove trianglebabyactornurseboyfriend girlfriend relationshipfriendfather daughter relationship
Period:
year 19821980s
Story:
gender disguisetelevision directortelevision producerlive televisiondrink thrown into someone's facemale actor playing a female characterunemployed actoractor playing female rolenurse capnurse costumenurse hatnurse uniformwine drinkinggirl in pantiesman wearing woman's clothing β€¦suspected of being gayfictional soap operaunanswered telephone callinferiority complexcorncobman kissing manshaving legssharing a bedunexpected kisstrue identity revealedacting teacheracting lessonactor's lifemilkingscreen testtheatrical agentman dressed as a womanboutiqueserenadecocktail partyfemale empowermenttv show in filmhouseguestcrossdresserimpersonatorsurprise partyreputationbudweiserunwanted kisscross dresserwoman in lingeriebabysittingshopplaywrightdouble lifeautographdragnew jobnannyfrustrationhit in the crotchsexismimpostorphoto shootfalse identitywomanizerimpersonationrehearsalblockbustertitle based on songelectronic music scorefarceanswering machinewaiterflirtingcross dressingpremarital sexfeminismscreamauditionwidowermarriage proposalroommatebirthday partyapologydisguisemanhattan new york cityalcoholtelevisionpianodrinktelephone callshowerpantiessingingtitle spoken by characterdancingcharacter name in titleone word title (See All)

Mrs. Doubtfire (1993)
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Mrs. Doubtfire (1993)

Eccentric actor Daniel Hillard is an amusing and caring father. But after a disastrous birthday party for his son, Daniel's wife Miranda draws the line and files a divorce. He can see his three children only once a week which doesn't sit well with him. Daniel also holds a job at a TV studio as a shi β€¦pping clerk under the recommendation of his liason. But when Miranda puts out an ad for a housekeeper, Daniel takes it upon himself to make a disguise as a Scottish lady named Mrs Doubtfire. And Daniel must also deal with Miranda's new boyfriend Stu Dunemyer. (Read More)

Subgenre:
cult film
Locations:
restaurant
Characters:
single motheractorfather daughter relationship
Story:
gender disguisemale actor playing a female characteractor playing female rolecrossdresserimpersonatordragnew jobnannyimpostorimpersonationblockbustercross dressingbirthday partydisguisetelevision β€¦title spoken by charactercharacter name in title (See All)

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Shakespeare In Love (1998)
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Shakespeare In Love (1998)

Will Shakespeare is a known but struggling poet, playwright and actor who not only has sold his next play to both Philip Henslow and Richard Burbidge but now faces a far more difficult problem: he is bereft of ideas and has yet to begin writing. He is in search of his muse, the woman who will inspir β€¦e him but all attempts fail him until he meets the beautiful Viola de Lesseps. She loves the theatre and would like nothing more than to take to the stage but is forbidden from doing so as only men can be actors. She is also a great admirer of Shakespeare's works. Dressing as a man and going by the name of Thomas Kent, she auditions and is ideal for a part in his next play. Shakespeare soon sees through her disguise and they begin a love affair, one they know cannot end happily for them as he is already married and she has been promised to the dour Lord Wessex. As the company rehearses his new play, Will and Viola's love is transferred to the written page leading to the masterpiece that is Romeo and Juliet. (Read More)

Themes:
love
Characters:
actresslove triangleactor
Story:
gender disguiseunwanted kissplaywrightautographdragrehearsalblockbusterfarcecross dressingpremarital sexscreamauditiondisguisedancingcharacter name in title

Swingers (1996)
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Swingers (1996)

This is a story about Mike, a guy who left his girl in New York when he came to LA to be a star. It's been six months since his girlfriend left him and he's not doing so good. So, his pal and some other friends try and get him back in the social scene and forget about his 6 year relationship.

Subgenre:
cult film
Themes:
unemploymentbreak upseductiondrinkingfriendshiplove
Locations:
nightclubrestaurantbarnew york city
Characters:
actressbabyactorboyfriend girlfriend relationshipfriend
Story:
womanizeranswering machinepremarital sexauditiondrinktelephone callpantiessingingdancingone word title

Alfie (2004) is one of the best movies like Tootsie (1982)
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Alfie (2004)

In Manhattan, the British limousine driver Alfie is surrounded by beautiful women, most of them clients, and he lives as a Don Juan, having one night stands with all of them and without any sort of commitment. His girl-friend and single-mother Julie is quite upset with the situation and his best fri β€¦ends are his colleague Marlon and his girl-friend Lonette. Alfie has a brief affair with Lonette, and the consequences of his act forces Alfie to reflect and wonder about his life style. (Read More)

Themes:
seductiondrinkingfriendship
Locations:
nightclubrestaurantbarnew york city
Characters:
single motherbabyboyfriend girlfriend relationshipfriend
Story:
womanizerflirtingpremarital sexbirthday partyapologymanhattan new york cityalcoholdrinkpantiessingingdancingcharacter name in titleone word title

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Wicker Park (2004)
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Wicker Park (2004)

Matthew, a young advertising executive in Chicago, puts his life and a business trip to China on hold when he thinks he sees Lisa, the love of his life who walked out on him without a word two years earlier, walking out of a restaurant one day. With a little help from his friend Luke, Matthew obsess β€¦ively and relentlessly tracks Lisa down and while doing so, runs into another young woman calling herself Lisa whom, unknown to Matthew, is an actress named Alex and may hold the key to Lisa's disappearance, and discovery. (Read More)

Themes:
drinkinglovefriendship
Locations:
restaurant
Characters:
cheating on one's girlfriendactressnursefriend
Story:
girl in pantiesfrustrationimpersonationrehearsalanswering machinepremarital sexshowerpantiestitle spoken by characterdancing

Nurse Betty (2000)
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Nurse Betty (2000)

A Kansas City waitress with dreams of becoming a nurse becomes delusional after seeing her no-good car salesman husband murdered. Becoming delusional from shock, she becomes convinced that she is the former fiancee of her soap opera idol. What she also believes is that the soap opera is real and goe β€¦s to LA to find the hospital where he works as a cardiologist. Meanwhile, her husband's murderers are searching for the drugs stolen by her husband and, as luck would have it, they are stored in the trunk of the car she drove off in. Freeman, an aging hit man planning his retirement after this job, also becomes delusional about the woman he is tracking. (Read More)

Subgenre:
cult film
Themes:
celebritydrinkingfriendship
Locations:
restaurantbar
Characters:
actressactornursefriendfather daughter relationship
Story:
nurse capnurse costumenurse hatnurse uniformfictional soap operaroommatetelevisiondrinktelephone callcharacter name in title

Show Me Love (1998)
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Show Me Love (1998)

Amal is a small insignificant town where nothing ever happens, where the latest trends are out of date when they get there. Young Elin has a bit of a bad reputation when it comes to guys, but the fact is that she is inexperienced in that matter. Another girl in her school, Agnes, is in love with her β€¦ but is too shy to do anything about it. For a number of reasons, Elin ends up at Agnes' birthday party as the only guest. They have a girl's night out together but after that Elin desperately avoids Agnes, refusing to even consider her own feelings toward Agnes. (Read More)

Subgenre:
cult film
Themes:
break upseductiondrinkinglove
Characters:
boyfriend girlfriend relationshipfather daughter relationship
Story:
reputationfrustrationsexismtitle based on songbirthday partyapologydrinktelephone callshowerpantiestitle spoken by character

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Boys Don't Cry (1999) is one of the best movies like Tootsie (1982)
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Boys Don't Cry (1999)

Based on actual events. Brandon Teena is the popular new guy in a tiny Nebraska town. He hangs out with the guys, drinking, cussing, and bumper surfing, and he charms the young women, who've never met a more sensitive and considerate young man. Life is good for Brandon, now that he's one of the guys β€¦ and dating hometown beauty Lana; however, he's forgotten to mention one important detail. It's not that he's wanted in another town for GTA and other assorted crimes, but that Brandon Teena was actually born a woman named Teena Brandon. When his best friends make this discovery, Brandon's life is ripped apart. (Read More)

Themes:
seductiondrinkingfriendship
Locations:
farmbar
Characters:
single motherboyfriend girlfriend relationshipfriend
Story:
gender disguiseunwanted kissdouble lifeimpostortitle based on songcross dressingbirthday partydisguisedrinkshower

All Good Things (2010)
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All Good Things (2010)

A love story and murder mystery based on the most notorious unsolved murder case in New York history. The original screenplay uses newly discovered facts, court records and speculation as the foundation for a story of family, obsession, love and loss.

Themes:
drinkinglovefriendship
Locations:
restaurantnew york city
Characters:
nursefriendfather daughter relationship
Period:
year 19821980s
Story:
man dressed as a womancrossdresserdouble lifeanswering machinecross dressingmarriage proposalbirthday partydisguisemanhattan new york citydrinktelephone callshowerpantiessingingdancing

Some Like It Hot (1959)
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Some Like It Hot (1959)

When two Chicago musicians, Joe and Jerry, witness the the St. Valentine's Day massacre, they want to get out of town and get away from the gangster responsible, Spats Colombo. They're desperate to get a gig out of town but the only job they know of is in an all-girl band heading to Florida. They sh β€¦ow up at the train station as Josephine and Daphne, the replacement saxophone and bass players. They certainly enjoy being around the girls, especially Sugar Kane Kowalczyk who sings and plays the ukulele. Joe in particular sets out to woo her while Jerry/Daphne is wooed by a millionaire, Osgood Fielding III. Mayhem ensues as the two men try to keep their true identities hidden and Spats Colombo and his crew show up for a meeting with several other crime lords. (Read More)

Subgenre:
cult film
Themes:
seductiondrinking
Characters:
love triangle
Story:
gender disguiseactor playing female roletheatrical agentsurprise partyrehearsalblockbusterfarcewaiterflirtingcross dressingmarriage proposalroommatedisguisedrinktelephone call β€¦pantiessingingtitle spoken by characterdancing (See All)

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Down With Love (2003)
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Down With Love (2003)

An homage to the early 1960s sex comedies that starred Rock Hudson and Doris Day. The story follows a best-selling female advice author who has all the answers until a sly journalist playboy starts asking the questions.

Themes:
seductiondrinkinglovefriendship
Locations:
new york city
Characters:
friend
Story:
false identitywomanizerimpersonationtitle based on songfarcefeminismmarriage proposalmanhattan new york citydrinksingingtitle spoken by character

Wedding Crashers (2005) is one of the best movies like Tootsie (1982)
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Wedding Crashers (2005)

Two friends, John (played by Owen Wilson) and Jeremy (Vince Vaughn), crash weddings to pick up women. One day they crash the wedding of the daughter of the Treasury Secretary, Secretary Cleary (Christopher Walken). Instead of short-term flings they end up being invited to the Clearys' island estate, β€¦ and potentially meet the loves of their lives... (Read More)

Themes:
seductiondrinkingfriendship
Characters:
cheating on one's girlfriendfriendfather daughter relationship
Story:
houseguestimpersonatorunwanted kissimpostorwomanizerimpersonationblockbusterwaiterflirtingpremarital sexmarriage proposalapologydrinktelephone callpanties β€¦dancing (See All)

Coyote Ugly (2000)
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Coyote Ugly (2000)

Sexy, romantic comedy about a girl in her early 20s named Violet Sanford going to NYC to pursue a dream of becoming a songwriter. Violet gets a "day" job as a bar maid at a nightclub called Coyote Ugly. Coyote Ugly is the city's newest hot spot where the employees are a team of sexy, resourceful wom β€¦en that provoke the clientele and press with their mischief. (Read More)

Themes:
friendship
Locations:
nightclubbarnew york city
Characters:
boyfriend girlfriend relationshipfather daughter relationship
Story:
girl in pantiesautographnew jobauditionmanhattan new york citypianopantiessingingdancing

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Jersey Girl (2004)
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Jersey Girl (2004)

Ollie Trinkie is a publicist, who has a great girlfriend, Gertrude, whom he marries and they are expecting a baby but while he is looking forward to being a father, he doesn't lighten his workload. Gertrude gives birth but dies in the process. Ollie doesn't live up to his responsibilities as a fathe β€¦r. Eventually the strain and pressure of losing his wife and being a father gets to him and he has breakdown, which leads to his termination. So with nothing much to do he tries to be good father to his daughter, Gertie. He also meets a young woman name Maya, who likes him but he is still not over his wife. (Read More)

Subgenre:
cult film
Themes:
unemploymentseductiondrinkingfriendship
Locations:
barnew york city
Characters:
babynursefriendfather daughter relationship
Story:
widowerapologymanhattan new york citypianodrinkshowerdancing

All About Eve (1950)
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All About Eve (1950)

Eve (Anne Baxter) is waiting backstage to meet her idol, aging Broadway star Margo Channing (Bette Davis). It seems innocent enough as Eve explains that she has seen Margo in EVERY performance of her current play. Only playwright/critic DeWitt (George Sanders) sees through Eve's evil plan, which is  β€¦to take her parts and her fiance, Bill Simpson (Gary Merrill). When the fiance shows no interest, she tries for playwright Lloyd Richards (Hugh Marlowe), but DeWitt stops her. After she accepts her award, she decides to skip the after-party and goes to her room, where a young woman named Phoebe has sneaked into her room and fallen asleep. This is where the "Circle of Life" now comes to fruition as Eve will get played like she played Margo. (Read More)

Themes:
drinkingfriendship
Locations:
restaurantnew york city
Characters:
actressactorfriend
Story:
playwrightrehearsalblockbusterwaiterauditionbirthday partyapologymanhattan new york citypianodrinktelephone calltitle spoken by charactercharacter name in title

Knocked Up (2007) is one of the best movies like Tootsie (1982)
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Knocked Up (2007)

When Alison Scott is promoted in E! Television, she goes to a night-club to celebrate with her older married sister Debbie. Alison meets the pothead reckless Ben Stone and while having a small talk with Ben, Debbie's husband Pete calls her to tell that their daughter has chicken pox. Debbie leaves t β€¦he place but Allison stays with Ben, drinking and dancing along all night; completely wasted, they end up having a one night stand. Ben does not use condom and eight weeks later, Allison discovers that she is pregnant. She calls Ben and they decide to try to stay together and have the baby. However, Ben needs to grow-up first to raise a family of his own. (Read More)

Themes:
unemploymentdrinkinglove
Locations:
nightclubrestaurantbar
Characters:
babyfriendfather daughter relationship
Story:
television producergirl in pantieshit in the crotchpremarital sexmarriage proposalroommatebirthday partypantiesdancing

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Dreamgirls (2006)
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Dreamgirls (2006)

Detroit, the early 1960s. Curtis Taylor, Jr., a car salesman, breaks into the music business with big dreams. He signs a trio of young women, the Dreamettes, gets them a job backing an R&B performer, James "Thunder" Early, establishes his own record label and starts wheeling and dealing. When Early  β€¦flames out, Curtis makes the Dreamettes into headliners as the Dreams, but not before demoting their hefty big-voiced lead singer, Effie White, and putting the softer-voiced looker, Deena Jones, in front. Soon after, he fires Effie, sends her into a life of proud poverty, and takes Deena and the Dreams to the top. How long can Curtis stay there, and will Effie ever get her due? (Read More)

Themes:
unemploymentcelebritydrinkingfriendshiplove
Locations:
nightclubbarnew york city
Characters:
cheating on one's girlfriendsingle motheractresslove trianglefriendfather daughter relationship
Story:
rehearsalauditionpianodrinktelephone callsingingtitle spoken by characterdancingone word title

Uptown Girls (2003)
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Uptown Girls (2003)

Molly Gunn, the freewheeling daughter of a deceased rock legend, is forced to get a job when her manager steals her money. As nanny for precocious Ray, the oft ignored daughter of a music executive, she learns what it means to be an adult while teaching Ray how to be a child.

Themes:
break upfriendship
Locations:
nightclubnew york city
Characters:
friend
Story:
nannytitle based on songfarcepremarital sexroommatebirthday partymanhattan new york citypanties

Sleeping With Other People (2015)
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Sleeping With Other People (2015)

Themes:
break updrinkingfriendship
Locations:
restaurantbar
Characters:
boyfriend girlfriend relationshipfriendfather daughter relationship
Story:
girl in pantieswomanizeranswering machinewaitermarriage proposalbirthday partyapologymanhattan new york citydrinktelephone callpantiestitle spoken by characterdancing

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Boogie Nights (1997) is one of the best movies like Tootsie (1982)
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Boogie Nights (1997)

Adult film director Jack Horner is always on the lookout for new talent and it's only by chance that he meets Eddie Adams who is working as a busboy in a restaurant. Eddie is young, good looking and plenty of libido to spare. Using the screen name Dirk Diggler, he quickly rises to the top of his ind β€¦ustry winning awards year after year. Drugs and ego however come between Dirk and those around him and he soon finds that fame is fleeting. (Read More)

Subgenre:
cult film
Themes:
drinkinglove
Locations:
nightclubrestaurant
Characters:
actressbabyactor
Period:
year 19821980s
Story:
girl in pantiesboutiqueunwanted kisstitle based on songwaiterapologyalcoholdrinktelephone callpantiessingingdancing

Confessions Of A Dangerous Mind (2002)
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Confessions Of A Dangerous Mind (2002)

Television made him famous, but his biggest hits happened off screen. "Confessions of a Dangerous Mind" is the story of a legendary showman's double life - television producer by day, CIA assassin by night. At the height of his TV career, Chuck Barris was recruited by the CIA and trained to become a β€¦ covert operative. Or so Barris said. (Read More)

Themes:
drinking
Locations:
restaurantbarnew york city
Period:
1980s
Story:
television producersurprise partydouble lifepremarital sexauditionmarriage proposalmanhattan new york citytelevisiondrinkshowersingingdancing

Lovelace (2013)
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Lovelace (2013)

Themes:
drinkingfriendship
Locations:
restaurantnew york city
Characters:
actressfriendfather daughter relationship
Story:
girl in pantiesautographphoto shootauditionmarriage proposalapologydrinktelephone callpantiessingingtitle spoken by characterdancingcharacter name in titleone word title

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Audition (1999)
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Audition (1999)

In Tokyo, Shigeharu Aoyama is a widower that grieves the loss of his wife and raises his son Shigehiko Aoyama alone. Seven years later, the teenage Shigehiko asks why his middle-aged father does not remarry and Shigeharu meets his friend Yasuhisa Yoshikawa, who is a film producer, and tells his inte β€¦ntion. However, Shigeharu has difficulties to approach to available women to date and Yasuhisa decide to organize a sham audition for casting the lead actress for the fake movie. They receive several portfolios of candidates and Shigeharu becomes obsessed by the gorgeous Asami Yamazaki. Despite the advice of the experienced Yasuhisa, Shigeharu calls Asami to date and he falls for her. But who is the mysterious Asami? (Read More)

Subgenre:
cult film
Themes:
drinkingfriendship
Locations:
restaurantbar
Characters:
actressnurseboyfriend girlfriend relationshipfriendfather daughter relationship
Story:
screamauditionwidowermarriage proposalpianodrinktelephone callpantiestitle spoken by characterdancingone word title

Rent (2005) is one of the best movies like Tootsie (1982)
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Rent (2005)

This rock opera tells the story of one year in the life of a group of bohemians struggling in modern day East Village New York. The story centers around Mark and Roger, two roommates. While a former tragedy has made Roger numb to life, Mark tries to capture it through his attempts to make a film. In β€¦ the year that follows, the group deals with love, loss, AIDS, and modern day life in one truly powerful story. (Read More)

Themes:
break updrinkinglovefriendship
Locations:
restaurantbarnew york city
Characters:
boyfriend girlfriend relationshipfriendfather daughter relationship
Period:
1980s
Story:
man wearing woman's clothingcross dresseranswering machinewaitercross dressingroommatemanhattan new york citydrinktelephone callsingingtitle spoken by characterdancingone word title

School Of Rock (2003)
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School Of Rock (2003)

Down and out rock star Dewey Finn gets fired from his band, and he faces a mountain of debts and depression. He takes a job as a 4th grade substitute teacher at an uptight private school where his attitude and hijinx have a powerful effect on his students. He also meets Zack, a 10-year-old guitar pr β€¦odigy, who could help Dewey win a "battle of the bands" competition, which would solve his financial problems and put him back in the spotlight. (Read More)

Subgenre:
cult film
Themes:
drinkingfriendship
Locations:
nightclubbar
Characters:
friend
Story:
impostorimpersonationrehearsalfarceroommateapologypianodrinktelephone callsingingtitle spoken by character

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American Wedding (2003)
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American Wedding (2003)

Jim Levenstein has finally found the courage to ask his girlfriend, Michelle Flaherty to marry him. She agrees to get married, but the problems don't stop there for Jim. Now along with Paul Finch and Kevin Myers, Jim must plan the wedding. Unfortunately Steve Stifler is in town and won't let the wed β€¦ding go past without having some fun himself, which includes setting up a secret bachelor party. (Read More)

Subgenre:
cult film
Themes:
drinkingfriendship
Locations:
restaurantbar
Characters:
love trianglefriendfather daughter relationship
Story:
girl in pantieshit in the crotchfarcewaiterpremarital sexmarriage proposalapologydrinktelephone callpantiesdancing

Reign Over Me (2007)
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Reign Over Me (2007)

Alan Johnson has everything he needs to get through life: a good job, a beautiful and loving wife, and their wonderful children. Yet he feels isolated because he finds having a hard-working job and managing a family too much to handle and has no one to talk to about it. Charlie Fineman, on the other β€¦ hand, doesn't have a job or a family. He used to have both until a terrible loss, and the grief caused him to quit his job and isolate himself from everyone around him. As it turns out, Alan and Charlie were roommates in college, and a chance encounter one night rekindles the friendship they shared. But when Charlie's problems become too much to deal with, Alan is determined to help Charlie come out of his emotional abyss. (Read More)

Themes:
seductiondrinkingfriendshiplove
Locations:
nightclubrestaurantbarnew york city
Characters:
friendfather daughter relationship
Story:
drink thrown into someone's facetitle based on songwidowerroommateapologymanhattan new york citydrinktelephone callsingingtitle spoken by character

Terms Of Endearment (1983) is one of the best movies like Tootsie (1982)
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Terms Of Endearment (1983)

Aurora and Emma are mother and daughter who march to different drummers. Beginning with Emma's marriage, Aurora shows how difficult and loving she can be. The movie covers several years of their lives as each finds different reasons to go on living and find joy. Aurora's interludes with Garrett Bree β€¦dlove, retired astronaut and next door neighbor are quite striking. In the end, different people show their love in very different ways. (Read More)

Themes:
break upfriendshiplove
Locations:
restaurantnew york city
Characters:
single motherbabyfriend
Story:
womanizerblockbusterflirtingpremarital sexbirthday partymanhattan new york city

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Something's Gotta Give (2003)
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Something's Gotta Give (2003)

Harry Sanborn is an aged music industry exec with a fondness for younger women like Marin, his latest trophy girlfriend. Things get a little awkward when Harry suffers a heart attack at the home of Marin's mother Erica. Left in the care of Erica and his doctor, a love triangle starts to take shape.

Themes:
drinkingfriendshiplove
Locations:
restaurantnew york city
Characters:
actresslove trianglebabynurseboyfriend girlfriend relationshipfather daughter relationship
Story:
playwrightflirtingfeminismmanhattan new york citydrinktelephone call

La La Land (2016)
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La La Land (2016)

Aspiring actress serves lattes to movie stars in between auditions and jazz musician Sebastian scrapes by playing cocktail-party gigs in dingy bars. But as success mounts, they are faced with decisions that fray the fragile fabric of their love affair, and the dreams they worked so hard to maintain  β€¦in each other threaten to rip them apart. (Read More)

Themes:
love
Locations:
nightclubbar
Characters:
actressbabyboyfriend girlfriend relationship
Story:
cocktail partyplaywrightphoto shootrehearsalauditionroommateapologypianotelephone callshowersingingdancing

Nine (2009)
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Nine (2009)

Arrogant, self-centered movie director Guido Contini finds himself struggling to find meaning, purpose, and a script for his latest film endeavor. With only a week left before shooting begins, he desperately searches for answers and inspiration from his wife, his mistress, his muse, and his mother.  β€¦As his chaotic profession steadily destroys his personal life, Guido must find a balance between creating art and succumbing to its obsessive demands. (Read More)

Themes:
seductiondrinking
Locations:
nightclubbar
Characters:
actresslove triangleactornurse
Story:
screen testautographwomanizerpianodrinktelephone callpantiessingingdancingone word title

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Notting Hill (1999) is one of the best movies like Tootsie (1982)
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Notting Hill (1999)

Every man's dream comes true for William Thacker, an unsuccessful Notting Hill bookstore owner, when Anna Scott, the world's most beautiful woman and best-liked actress, enters his shop. A little later, he still can't believe it himself, William runs into her again - this time spilling orange juice  β€¦over her. Anna accepts his offer to change in his nearby apartment, and thanks him with a kiss, which seems to surprise her even more than him. Eventually, Anna and William get to know each other better over the months, but being together with the world's most wanted woman is not easy - neither around your closest friends, nor in front of the all-devouring press. (Read More)

Themes:
celebrityfriendship
Characters:
actressfriend
Story:
wine drinkingshopimpostorblockbusterroommatebirthday partytelephone calltitle spoken by character

Giant (1956)
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Giant (1956)

Texan rancher Bick Benedict visits a Maryland farm to buy a prize horse. Whilst there he meets and falls in love with the owner's daughter Leslie, they are married immediately and return to his ranch. The story of their family and its rivalry with cowboy and (later oil tycoon) Jett Rink unfolds acro β€¦ss two generations. (Read More)

Themes:
drinkingfriendshiplove
Locations:
farmrestaurantbar
Characters:
actresslove trianglebabynursefriendfather daughter relationship
Story:
babysittingsexismblockbusterwaitermarriage proposalbirthday partydrinktelephone callsingingone word title

The Producers (1967)
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The Producers (1967)

Down-on-his-luck theatrical producer Max Bialystock is forced to romance rich old ladies to finance his efforts. When timid accountant Leo Bloom reviews Max's accounting books, the two hit upon a way to make a fortune by producing a sure-fire flop. The play which is to be their gold mine? "Springtim β€¦e for Hitler." (Read More)

Subgenre:
cult film
Locations:
restaurantbarnew york city
Characters:
actor
Story:
playwrightrehearsalfarceflirtingcross dressingauditionmanhattan new york citysingingdancing

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She's The Man (2006)
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She's The Man (2006)

Here's the thing! Viola's soccer team at Cornwall gets cut. She wants to join the boys team, but they do not allow girls. So she thinks "If you can't join them, beat them". So she does! She disguises herself as her twin brother Sebastian, and goes out for the rival school, Illyria, boys' soccer team β€¦ and makes it. Unfortunately, she didn't plan falling in love with her roommate Duke. But Duke has his eyes on Olivia. What makes matters worse is that Olivia starts to fall for Sebastian because he/she has a sensitive side. If things couldn't get more problematic, the real Sebastian (who was in London working on his music) comes home early. He arrives on campus and has no clue that he was replaced by his twin sister. (Read More)

Themes:
break upfriendshiplove
Characters:
love trianglefather daughter relationship
Story:
gender disguisecrossdressersexismimpersonationflirtingcross dressingroommatedisguiseshower

The Sweetest Thing (2002) is one of the best movies like Tootsie (1982)
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The Sweetest Thing (2002)

To ease their roommate through a relationship-induced depression, Christina Walters and Courtney Rockcliffe take her out on the town. During their attempts to find her "Mr. Right Now", Christina meets Peter Donahue. Missing her opportunity with him that night, Christina is talked into pursuing him t β€¦o his brother's wedding. (Read More)

Themes:
break upfriendship
Locations:
nightclub
Characters:
boyfriend girlfriend relationship
Story:
girl in pantiesboutiquetitle based on songflirtingroommatepantiessingingtitle spoken by characterdancing

Forgetting Sarah Marshall (2008)
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Forgetting Sarah Marshall (2008)

Peter is a composer and a likable sad sack who's devastated when his girlfriend of five years, Sarah Marshall, the star of a cheesy CSI-style crime show, dumps him. He weeps, he rails, he mopes. Finally, his step-brother Brian suggests Hawaii, so Peter heads for a resort on Oahu where, as he's check β€¦ing in, he sees Sarah and her new beau, Aldous, a polymorphously perverse English rocker. The weeping and moping start again, until Peter is rescued by Rachel, a thoughtful hotel clerk who invites him to a luau and to hang out. Although he constantly runs into Sarah and Aldous, Peter starts to come alive again. Will Sarah realize what she's lost, and what about Rachel? (Read More)

Themes:
drinkingfriendship
Locations:
restaurantbar
Characters:
actressboyfriend girlfriend relationshipfriend
Story:
tv show in filmwaiterflirtingpremarital sexmarriage proposalapologypianodrinktelephone callshowersingingcharacter name in title

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A Night At The Opera (1935)
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A Night At The Opera (1935)

The Marx Brothers take on high society. Two lovers who are both in opera are prevented from being together by the man's lack of acceptance as an operatic tenor. Pulling several typical Marx Brothers' stunts, they arrange for the normal tenor to be absent so that the young lover can get his chance.

Locations:
restaurant
Story:
serenadedragimpostorrehearsalfarcewaitercross dressingdisguisepianopantiessingingdancing

Catch Me If You Can (2002)
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Catch Me If You Can (2002)

New Rochelle, the 1960s. High schooler Frank Abagnale Jr. idolizes his father, who's in trouble with the IRS. When his parents separate, Frank runs away to Manhattan with $25 in his checking account, vowing to regain dad's losses and get his parents back together. Just a few years later, the FBI tra β€¦cks him down in France; he's extradited, tried, and jailed for passing more than $4,000,000 in bad checks. Along the way, he's posed as a Pan Am pilot, a pediatrician, and an attorney. And, from nearly the beginning of this life of crime, he's been pursued by a dour FBI agent, Carl Hanratty. What starts as cat and mouse becomes something akin to father and son. (Read More)

Subgenre:
cult film
Locations:
restaurantbarnew york city
Characters:
nurseboyfriend girlfriend relationshipfather daughter relationship
Story:
impersonatornew jobimpostorwomanizerimpersonationblockbusterwaiterpremarital sexauditionmarriage proposaldisguisemanhattan new york citysingingdancing

A Hard Day's Night (1964) is one of the best movies like Tootsie (1982)
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A Hard Day's Night (1964)

The Beatles--the world's most famous rock and roll band--travel from their home town of Liverpool to London to perform in a television broadcast. Along the way they must rescue Paul's unconventional grandfather from various misadventures and drummer Ringo goes missing just before the crucial concert β€¦. (Read More)

Subgenre:
cult film
Locations:
nightclub
Story:
television directortheatrical agentautographrehearsaltitle based on songdisguisetelevisionpianodancing

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My Left Foot (1989)
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My Left Foot (1989)

Christy Brown is a spastic quadriplegic born to a large, poor Irish family. His mother, Mrs Brown, recognizes the intelligence and humanity in the lad everyone else regards as a vegetable. Eventually, Christy matures into a cantankerous writer who uses his only functional limb, his left foot, to wri β€¦te with. (Read More)

Themes:
unemploymentdrinkinglove
Locations:
restaurant
Characters:
babynursefather daughter relationship
Story:
frustrationflirtingmarriage proposalbirthday partyapologydrinktelephone callsingingcharacter name in title

Kiss Kiss Bang Bang (2005)
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Kiss Kiss Bang Bang (2005)

A petty thief posing as an actor is brought to Los Angeles for an unlikely audition and finds himself in the middle of a murder investigation along with his high school dream girl and a detective who's been training him for his upcoming role...

Subgenre:
cult film
Themes:
drinkingfriendship
Locations:
nightclubbarnew york city
Characters:
actressactorboyfriend girlfriend relationshipfriendfather daughter relationship
Story:
girl in pantiesscreen testcross dressingauditionmanhattan new york citydrinkpanties

The Graduate (1967)
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The Graduate (1967)

Ben has recently graduated from college, with his parents now expecting great things from him. At his "Homecoming" party, Mrs. Robinson, the wife of his father's business partner, has Ben drive her home, which leads to an affair between the two. The affair eventually ends, but comes back to haunt hi β€¦m when he finds himself falling for Elaine, Mrs. Robinson's daughter. (Read More)

Subgenre:
cult film
Themes:
break upseductiondrinking
Locations:
bar
Characters:
love triangleboyfriend girlfriend relationshipfather daughter relationship
Story:
blockbusterscreammarriage proposalbirthday partyapologydrinktelephone call

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Dan In Real Life (2007) is one of the best movies like Tootsie (1982)
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Dan In Real Life (2007)

Single father Dan Burns dedicates his life to his children, but one day he meets Marie at a bookstore. They get to know each other, but then Dan finds out that Marie is actually dating his brother, Mitch.

Themes:
break up
Locations:
restaurantnew york city
Characters:
love triangleboyfriend girlfriend relationshipfather daughter relationship
Story:
frustrationwidowerapologypianotelephone callshowersingingdancingcharacter name in title

Eyes Wide Shut (1999)
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Eyes Wide Shut (1999)

After his wife, Alice, tells him about her sexual fantasies, William Harford sets out for a night of sexual adventure. After several less than successful encounters, he meets an old friend, Nick Nightingale - now a musician - who tells him of strange sex parties when he is required to play the piano β€¦ blindfolded. All the men at the party are costumed and wear masks while the women are all young and beautiful. Harford manages to find an appropriate costume and heads out to the party. Once there, however, he is warned by someone who recognizes him, despite the mask, that he is in great danger. He manages to extricate himself but the threats prove to be quite real and sinister. (Read More)

Subgenre:
cult film
Themes:
drinkingfriendship
Locations:
restaurantnew york city
Characters:
nurseboyfriend girlfriend relationshipfriendfather daughter relationship
Story:
girl in pantiesfrustrationflirtingroommatedisguisemanhattan new york citypianodrinktelephone callpantiesdancing

Bridesmaids (2011)
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Bridesmaids (2011)

Annie (Kristen Wiig), is a maid of honor whose life unravels as she leads her best friend, Lillian (Maya Rudolph), and a group of colorful bridesmaids (Rose Byrne, Melissa McCarthy, Wendi McLendon-Covey and Ellie Kemper) on a wild ride down the road to matrimony. Annie's life is a mess. But when she β€¦ finds out her lifetime best friend is engaged, she simply must serve as Lillian's maid of honor. Though lovelorn and broke, Annie bluffs her way through the expensive and bizarre rituals. With one chance to get it perfect, she'll show Lillian and her bridesmaids just how far you'll go for someone you love. (Read More)

Themes:
drinkinglovefriendship
Locations:
restaurantbar
Characters:
friend
Story:
girl in pantieswoman in lingeriefrustrationimpersonationflirtingroommateapologyalcoholdrinktelephone callpantiessingingtitle spoken by characterone word title

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I'm Not There (2007)
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I'm Not There (2007)

Six incarnations of Bob Dylan: an actor, a folk singer, an electrified troubadour, Rimbaud, Billy the Kid, and Woody Guthrie. Put Dylan's music behind their adventures, soliloquies, interviews, marriage, and infidelity. Recreate 1960s documentaries in black and white. Put each at a crossroads, the a β€¦rtist becoming someone else. Jack, the son of Ramblin' Jack Elliott, finds Jesus; handsome Robbie falls in love then abandons Claire. Woody, a lad escaped from foster care, hobos the U.S. singing; Billy awakes in a valley threatened by a six-lane highway; Rimbaud talks. Jude, booed at Newport when he goes electric, fences with reporters, pundits, and fans. He won't be classified. (Read More)

Subgenre:
cult film
Themes:
break upcelebritydrinkinglove
Locations:
restaurantbarnew york city
Characters:
babyactornursefather daughter relationship
Story:
title based on songfeminismmanhattan new york citypianodrinktelephone callpantiessingingdancing

Scott Pilgrim Vs. The World (2010) is one of the best movies like Tootsie (1982)
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Scott Pilgrim Vs. The World (2010)

Scott Pilgrim plays in a band which aspires to success. He dates Knives Chau, a high-school girl five years younger, and he hasn't recovered from being dumped by his former girlfriend, now a success with her own band. When Scott falls for Ramona Flowers, he has trouble breaking up with Knives and tr β€¦ies to romance Ramona. As if juggling two women wasn't enough, Ramona comes with baggage: seven ex-lovers, with each of whom Scott must do battle to the death in order to win Ramona. (Read More)

Subgenre:
cult film
Themes:
unemploymentbreak updrinkingfriendship
Locations:
nightclubbar
Characters:
actorboyfriend girlfriend relationshipfriend
Story:
girl in pantiessharing a bedautographelectronic music scoreroommateapologypantiessingingcharacter name in title

Annie Hall (1977)
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Annie Hall (1977)

Alvy Singer, a forty year old twice divorced, neurotic, intellectual Jewish New York stand-up comic, reflects on the demise of his latest relationship, to Annie Hall, an insecure, flighty, Midwestern WASP aspiring nightclub singer. Unlike his previous relationships, Alvy believed he may have worked  β€¦out all the issues in his life through fifteen years of therapy to make this relationship with Annie last, among those issues being not wanting to date any woman that would want to date him, and thus subconsciously pushing those women away. Alvy not only reviews the many ups and many downs of their relationship, but also reviews the many facets of his makeup that led to him starting to date Annie. Those facets include growing up next to Coney Island in Brooklyn, being attracted to the opposite sex for as long as he can remember, and enduring years of Jewish guilt with his constantly arguing parents. (Read More)

Themes:
break up
Locations:
nightclubbarnew york city
Characters:
actor
Story:
cocktail partyunwanted kissautographrehearsalflirtingpremarital sexmarriage proposaltitle spoken by charactercharacter name in title

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