The Best 'Complex's 50 Worst Romantic Comedies' Movies

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Held position in the past 45 days

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2

You've Got Mail 1998, 119 min.

Nora Ephron     Starring: Tom HanksGreg KinnearParker Posey

Comedy    Female-Directed Film    Romance

Down by 1 in the past 45 days 1

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3

Chances Are 1989, 108 min.

Emile Ardolino     Starring: Cybill ShepherdRobert Downey Jr.Ryan O'Neal

Comedy    Fantasy Comedy    Fantasy

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Down by 1 in the past 45 days 1

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Held position in the past 45 days

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7

Runaway Bride 1999, 116 min.

Garry Marshall     Starring: Joan CusackJulia RobertsRichard Gere

Comedy    Romance    Romantic Comedy

Down by 1 in the past 45 days 1

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Up by 2 in the past 45 days 2

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9

Blame It on Rio 1984, 100 min.

Stanley Donen     Starring: Michael CaineJoseph BolognaValerie Harper

Comedy    Farce    Sex Comedy

Down by 1 in the past 45 days 1

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10

Chasing Liberty 2004, 111 min.

Andy Cadiff     Starring: Mandy MooreMark HarmonRobert Ashe

Comedy    Road Movie    Romance

Held position in the past 45 days

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11

Simply Irresistible 1999, 94 min.

Mark Tarlov     Starring: Patricia ClarksonDylan BakerBetty Buckley

Comedy    Fantasy    Romance

Down by 51 in the past 45 days 51

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Up by 1 in the past 45 days 1

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17

Summer Catch 2001, 108 min.

Michael Tollin     Starring: Matthew LillardFreddie Prinze Jr.Brian Dennehy

Comedy Drama    Drama    Romance

Down by 1 in the past 45 days 1

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18

Good Luck Chuck 2007, 101 min.

Mark Helfrich     Starring: Dane CookJessica AlbaEllia English

Comedy    Romance    Romantic Comedy

Held position in the past 45 days

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19

Employee of the Month 2006, 103 min.

Greg Coolidge     Starring: Dane CookJessica SimpsonAndy Dick

Comedy    Romance    Romantic Comedy

Up by 19 in the past 45 days 19

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