The Top 100 Romantic Comedies of All Time

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1

City Lights 1931, 87 min.

Charles Chaplin     Starring: Charles ChaplinVirginia CherrillFlorence Lee

Comedy Drama    Comedy    Drama

Held position in the past 45 days

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2

The Apartment 1960, 125 min.

Billy Wilder     Starring: Jack LemmonFred MacMurrayRay Walston

Comedy Drama    Drama    Romance

Held position in the past 45 days

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8

Groundhog Day 1993, 101 min.

Harold Ramis     Starring: Bill MurrayAndie MacDowellChris Elliott

Comedy    Fantasy Comedy    Fantasy

Held position in the past 45 days

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9

Annie Hall 1977, 93 min.

Woody Allen     Starring: Woody AllenDiane KeatonTony Roberts

Comedy of Manners    Comedy    New Hollywood

Held position in the past 45 days

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Held position in the past 45 days

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11

Manhattan 1979, 96 min.

Woody Allen     Starring: Woody AllenDiane KeatonMichael Murphy

Comedy Drama    Comedy of Manners    Drama

Held position in the past 45 days

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Held position in the past 45 days

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15

Roman Holiday 1953, 118 min.

William Wyler     Starring: Audrey HepburnGregory PeckEddie Albert

Comedy    Romance    Romantic Comedy

Down by 1 in the past 45 days 1

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25

Sabrina 1954, 113 min.

Billy Wilder     Starring: Humphrey BogartAudrey HepburnWilliam Holden

Comedy Drama    Romance    Romantic Comedy

Held position in the past 45 days

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26

Big 1988, 104 min.

Penny Marshall     Starring: Robert LoggiaElizabeth PerkinsJared Rushton

Comedy    Fantasy Comedy    Fantasy

Held position in the past 45 days

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27

Ninotchka 1939, 110 min.

Ernst Lubitsch     Starring: Greta GarboMelvyn DouglasIna Claire

Comedy    Romance    Romantic Comedy

Held position in the past 45 days

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Down by 2 in the past 45 days 2

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29

The Quiet Man 1952, 129 min.

John Ford     Starring: John WayneVictor McLaglenBarry Fitzgerald

Comedy Drama    Drama    Romance

Held position in the past 45 days

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30

High Fidelity 2000, 113 min.

Stephen Frears     Starring: John CusackIben HjejleTodd Louiso

Comedy Drama    Comedy of Manners    Romance

Held position in the past 45 days

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31

Say Anything... 1989, 100 min.

Cameron Crowe     Starring: John CusackIone SkyeJohn Mahoney

Comedy Drama    Coming-of-Age    Romance

Held position in the past 45 days

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Held position in the past 45 days

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39

Holiday 1938, 95 min.

George Cukor     Starring: Katharine HepburnCary GrantDoris Nolan

Based-on-Theatre    Comedy    Domestic Comedy

Down by 7 in the past 45 days 7

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42

Broadcast News 1987, 133 min.

James L. Brooks     Starring: William HurtJoan CusackAlbert Brooks

Comedy Drama    Media Satire    Romance

Down by 1 in the past 45 days 1

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43

Bull Durham 1988, 108 min.

Ron Shelton     Starring: Susan SarandonJenny RobertsonKevin Costner

Comedy    Romance    Romantic Comedy

Down by 1 in the past 45 days 1

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44

Midnight in Paris 2011, 94 min.

Woody Allen     Starring: Owen WilsonRachel McAdamsMarion Cotillard

Comedy    Fantasy    Magic Realism

Held position in the past 45 days

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47

Juno 2007, 96 min.

Jason Reitman     Starring: Ellen PageMichael CeraJennifer Garner

Comedy Drama    Coming-of-Age    Domestic Comedy

Held position in the past 45 days

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Up by 1 in the past 45 days 1

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Held position in the past 45 days

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50

Adam's Rib 1949, 101 min.

George Cukor     Starring: Spencer TracyKatharine HepburnJudy Holliday

Comedy    Romance    Romantic Comedy

Held position in the past 45 days

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51

Defending Your Life 1991, 112 min.

Albert Brooks     Starring: Albert BrooksMeryl StreepRip Torn

Comedy    Fantasy Comedy    Fantasy

Up by 1 in the past 45 days 1

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52

Swingers 1996, 96 min.

Doug Liman     Starring: Vince VaughnPatrick Van HornBrooke Langton

Buddy Film    Comedy of Manners    Comedy

Held position in the past 45 days

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53

When Harry Met Sally... 1989, 96 min.

Rob Reiner     Starring: Billy CrystalMeg RyanCarrie Fisher

Comedy Drama    Drama    Romance

Held position in the past 45 days

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55

Up in the Air 2009, 109 min.

Jason Reitman     Starring: George ClooneyVera FarmigaAnna Kendrick

Comedy Drama    Drama    Family Drama

Down by 1 in the past 45 days 1

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58

Jerry Maguire 1996, 139 min.

Cameron Crowe     Starring: Tom CruiseCuba Gooding Jr.Renée Zellweger

Comedy Drama    Drama    Romance

Held position in the past 45 days

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60

Knocked Up 2007, 129 min.

Judd Apatow     Starring: Seth RogenKatherine HeiglPaul Rudd

Comedy    Romance    Romantic Comedy

Down by 1 in the past 45 days 1

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61

Out of Sight 1998, 123 min.

Steven Soderbergh     Starring: George ClooneyVing RhamesDon Cheadle

Caper    Comedy    Crime

Held position in the past 45 days

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62

Chasing Amy 1997, 113 min.

Kevin Smith     Starring: Joey Lauren AdamsJason MewesKevin Smith

Comedy Drama    Romance    Romantic Comedy

Held position in the past 45 days

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64

As Good As It Gets 1997, 139 min.

James L. Brooks     Starring: Jack NicholsonHelen HuntGreg Kinnear

Comedy Drama    Drama    Romance

Held position in the past 45 days

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66

Garden State 2004, 102 min.

Zach Braff     Starring: Natalie PortmanIan HolmZach Braff

Comedy Drama    Coming-of-Age    Reunion Films

Held position in the past 45 days

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Down by 1 in the past 45 days 1

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Down by 2 in the past 45 days 2

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71

How to Steal a Million 1966, 123 min.

William Wyler     Starring: Hugh GriffithEli WallachPeter O'Toole

Caper    Comedy    Crime

Down by 1 in the past 45 days 1

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74

Seven Chances 1925, 56 min.

Buster Keaton     Starring: Buster KeatonT. Roy BarnesSnitz Edwards

Comedy of Errors    Comedy    Romance

Up by 1 in the past 45 days 1

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75

Wedding Crashers 2005, 119 min.

David Dobkin     Starring: Owen WilsonVince VaughnChristopher Walken

Comedy    Farce    Romance

Held position in the past 45 days

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76

Funny Face 1957, 103 min.

Stanley Donen     Starring: Audrey HepburnFred AstaireKay Thompson

Comedy    Musical    Musical Comedy

Down by 1 in the past 45 days 1

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Down by 2 in the past 45 days 2

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79

About Time 2013, 123 min.

Richard Curtis     Starring: Domhnall GleesonRachel McAdamsBill Nighy

Comedy Drama    Drama    Fantasy

Held position in the past 45 days

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Up by 1 in the past 45 days 1

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82

Something Wild 1986, 113 min.

Jonathan Demme     Starring: Jeff DanielsMelanie GriffithRay Liotta

Comedy Drama    Drama    Road Movie

Down by 1 in the past 45 days 1

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Held position in the past 45 days

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84

I Love You, Man 2009, 105 min.

John Hamburg     Starring: Paul RuddRashida JonesJason Segel

Buddy Film    Comedy    Romance

Held position in the past 45 days

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85

Beginners 2010, 105 min.

Mike Mills     Starring: Ewan McGregorChristopher PlummerMelanie Laurent

Comedy Drama    Drama    Romance

Held position in the past 45 days

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Held position in the past 45 days

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87

Moonstruck 1987, 102 min.

Norman Jewison     Starring: CherNicolas CageVincent Gardenia

Comedy    Domestic Comedy    Romance

Held position in the past 45 days

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90

Beautiful Girls 1996, 112 min.

Ted Demme     Starring: Matt DillonMira SorvinoUma Thurman

Comedy Drama    Coming-of-Age    Ensemble Film

Down by 2 in the past 45 days 2

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91

Roxanne 1987, 107 min.

Fred Schepisi     Starring: Steve MartinDaryl HannahRick Rossovich

Comedy    Romance    Romantic Comedy

Down by 1 in the past 45 days 1

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94

About a Boy 2002, 101 min.

Chris Weitz     Starring: Hugh GrantNicholas HoultToni Collette

Comedy Drama    Coming-of-Age    Drama

Held position in the past 45 days

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95

L.A. Story 1991, 95 min.

Mick Jackson     Starring: Steve MartinVictoria TennantMarilu Henner

Comedy    Magic Realism    Romance

Held position in the past 45 days

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Held position in the past 45 days

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97

The Sure Thing 1985, 100 min.

Rob Reiner     Starring: John CusackBoyd GainesTim Robbins

Comedy    Coming-of-Age    Road Movie

Held position in the past 45 days

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98

Silver Streak 1976, 114 min.

Arthur Hiller     Starring: Gene WilderJill ClayburghRichard Pryor

Action    Buddy Film    Comedy

Down by 3 in the past 45 days 3

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100

Pretty Woman 1990, 125 min.

Garry Marshall     Starring: Richard GereJulia RobertsRalph Bellamy

Comedy    Prostitution Film    Romance

Held position in the past 45 days

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