99		Sex and the City (Comedy, Drama, Romance, 2008)
99		American Wedding (Comedy, Romance, 2003)
99		The Last Kiss (Comedy, Drama, Romance, 2006)
99		Miss Pettigrew Lives for a Day (Comedy, Romance, 2008)
99		Good Luck Chuck (Comedy, Romance, 2007)
99		The 40-Year-Old Virgin (Comedy, Romance, 2005)
99		The Sweetest Thing (Comedy, Romance, 2002)
99		The Big Bounce (Comedy, Crime, 2004)
99		Friends with Benefits (Comedy, Romance, 2011)
99		Malèna (Comedy, Drama, Romance, 2000)
99		The Change-Up (Comedy, Fantasy, 2011)
98		Sideways (Adventure, Comedy, Drama, 2004)
98		Hall Pass (Comedy, Romance, 2011)
97		YPF (Comedy, Drama, Romance, 2007)
96		Les poupées russes (Comedy, Drama, Romance, 2005)
95		Bachelor Party (Comedy, 1984)
92		100 Girls (Comedy, Romance, 2000)
92		Working Girl (Comedy, Drama, Romance, 1988)
89		Couples Retreat (Comedy, 2009)
88		Just Married (Comedy, Romance, 2003)
88		American Reunion (Comedy, 2012)
87		Cashback (Comedy, Drama, Romance, 2006)
85		Harold & Kumar Escape from Guantanamo Bay (Adventure, Comedy, 2008)
85		The House Bunny (Comedy, Romance, 2008)
85		Wedding Daze (Comedy, Romance, 2006)
84		The Ugly Truth (Comedy, Romance, 2009)
82		Forgetting Sarah Marshall (Comedy, Drama, Romance, 2008)
80		Used Cars (Comedy, 1980)
80		Made of Honor (Comedy, Romance, 2008)
80		Love and Other Disasters (Comedy, Romance, 2006)
79		The Door in the Floor (Comedy, Drama, 2004)
79		Fired Up! (Comedy, 2009)
79		Harold & Kumar Go to White Castle (Adventure, Comedy, 2004)
77		About Last Night... (Comedy, Drama, Romance, 1986)
77		Someone Like You... (Comedy, Romance, 2001)
75		L'auberge espagnole (Comedy, Drama, Romance, 2002)
74		Going the Distance (Comedy, Romance, 2010)
74		Private Parts (Biography, Comedy, Drama, 1997)
74		Funny People (Comedy, Drama, 2009)
73		The Dukes of Hazzard (Action, Adventure, Comedy, 2005)
73		What's Your Number? (Comedy, Romance, 2011)
72		One Night at McCool's (Comedy, Crime, 2001)
72		Weird Science (Comedy, Romance, Sci-Fi, 1985)
72		Married to the Mob (Comedy, Crime, Romance, 1988)
72		The Whole Nine Yards (Comedy, Crime, 2000)
71		Tamara Drewe (Comedy, Drama, Romance, 2010)
70		Porky's (Comedy, 1981)
70		Zack and Miri Make a Porno (Comedy, Romance, 2008)
70		Mallrats (Comedy, Romance, 1995)
69		Nutty Professor II: The Klumps (Comedy, Romance, Sci-Fi, 2000)
69		Wedding Crashers (Comedy, Romance, 2005)
69		Empire Records (Comedy, Drama, Music, 1995)
68		A Very Harold & Kumar 3D Christmas (Adventure, Comedy, 2011)
67		Road Trip (Adventure, Comedy, 2000)
67		American Pie 2 (Comedy, 2001)
67		Venus (Comedy, Drama, Romance, 2006)
67		Almost Famous (Adventure, Comedy, Drama, 2000)
67		We're the Millers (Comedy, Crime, 2013)
66		Spanglish (Comedy, Drama, Romance, 2004)
66		Factotum (Comedy, Drama, Romance, 2005)
66		Dirty Grandpa (Comedy, 2016)
65		Terms of Endearment (Comedy, Drama, 1983)
65		Revenge of the Nerds (Comedy, 1984)
65		Meet Bill (Comedy, Drama, 2007)
65		Fast Times at Ridgemont High (Comedy, Drama, 1982)
64		EuroTrip (Comedy, 2004)
64		To Die For (Comedy, Crime, Drama, 1995)
63		Take This Waltz (Comedy, Drama, 2011)
63		The Dictator (Comedy, Romance, 2012)
63		This Is 40 (Comedy, Romance, 2012)
63		The Ice Harvest (Comedy, Crime, Drama, 2005)
62		The Sure Thing (Comedy, Drama, Romance, 1985)
62		Wet Hot American Summer (Comedy, Romance, 2001)
62		Splash (Comedy, Fantasy, Romance, 1984)
62		Grind (Adventure, Comedy, Sport, 2003)
61		There's Something About Mary (Comedy, Romance, 1998)
61		The Girl Next Door (Comedy, Drama, Romance, 2004)
61		Rumor Has It... (Comedy, Drama, Romance, 2005)
60		The War of the Roses (Comedy, Romance, 1989)
59		Risky Business (Comedy, Crime, Drama, 1983)
58		Anger Management (Comedy, 2003)
58		The Wolf of Wall Street (Biography, Comedy, Crime, 2013)
58		Drop Dead Gorgeous (Comedy, Romance, Thriller, 1999)
57		The Big Wedding (Comedy, 2013)
57		Lymelife (Comedy, Drama, Romance, 2008)
57		Walk of Shame (Comedy, 2014)
56		Super Troopers (Comedy, Crime, Mystery, 2001)
56		D.E.B.S. (Action, Comedy, Romance, 2004)
56		He's Just Not That Into You (Comedy, Drama, Romance, 2009)
56		Forces of Nature (Comedy, Romance, 1999)
56		Bridget Jones: The Edge of Reason (Comedy, Drama, Romance, 2004)
55		Beerfest (Comedy, 2006)
55		27 Dresses (Comedy, Romance, 2008)
55		Roxanne (Comedy, Romance, 1987)
55		Take Me Home Tonight (Comedy, Drama, Romance, 2011)
54		A Dirty Shame (Comedy, 2004)
54		White Chicks (Comedy, Crime, 2004)
54		Little Fockers (Comedy, Romance, 2010)
54		Meet the Fockers (Comedy, Romance, 2004)
54		Along Came Polly (Comedy, Romance, 2004)
54		Get Him to the Greek (Comedy, Music, 2010)
53		Man Up (Comedy, Drama, Romance, 2015)
53		Goon (Comedy, Sport, 2011)
53		Movie 43 (Comedy, Romance, 2012)
53		Igby Goes Down (Comedy, Drama, 2002)
53		Husbands and Wives (Comedy, Drama, Romance, 1992)
52		Legally Blonde (Comedy, Romance, 2001)
52		The Jane Austen Book Club (Comedy, Drama, Romance, 2007)
52		Tootsie (Comedy, Drama, Romance, 1982)
52		Caddyshack (Comedy, Romance, Sport, 1980)
52		The Man with Two Brains (Comedy, Romance, Sci-Fi, 1983)
52		Rushmore (Comedy, Drama, 1998)
52		Wild at Heart (Comedy, Crime, Romance, 1990)
52		Jerry Maguire (Comedy, Drama, Romance, 1996)
52		I Think I Love My Wife (Comedy, Drama, Romance, 2007)
51		The Kids Are All Right (Comedy, Drama, Romance, 2010)
51		Birthday Girl (Comedy, Crime, Thriller, 2001)
51		In Her Shoes (Comedy, Drama, Romance, 2005)
50		Night Shift (Comedy, 1982)
50		Revenge of the Nerds II: Nerds in Paradise (Comedy, 1987)
49		Bridget Jones's Diary (Comedy, Drama, Romance, 2001)
49		2 Days in the Valley (Comedy, Crime, Thriller, 1996)
49		Storytelling (Comedy, Drama, Romance, 2001)
49		Whatever Works (Comedy, Romance, 2009)
48		Taking Woodstock (Comedy, Drama, Music, 2009)
48		Magic Mike (Comedy, Drama, 2012)
48		Sweet Home Alabama (Comedy, Romance, 2002)
48		The Story of Us (Comedy, Drama, Romance, 1999)
48		The Other Sister (Comedy, Drama, Romance, 1999)
48		Cedar Rapids (Comedy, 2011)
48		Sleeping with Other People (Comedy, Drama, Romance, 2015)
48		Young Adult (Comedy, Drama, 2011)
48		Fanboys (Adventure, Comedy, Drama, 2009)
47		Fools Rush In (Comedy, Drama, Romance, 1997)
47		New York, I Love You (Comedy, Drama, Romance, 2008)
47		Moonstruck (Comedy, Drama, Romance, 1987)
47		Cry-Baby (Comedy, Musical, Romance, 1990)
47		Son in Law (Comedy, Drama, Romance, 1993)
46		First Daughter (Comedy, Drama, Romance, 2004)
46		Killers (Action, Comedy, Romance, 2010)
46		Being Julia (Comedy, Drama, Romance, 2004)
46		Beginners (Comedy, Drama, Romance, 2010)
46		Human Nature (Comedy, Drama, Mystery, 2001)
46		Ride Along 2 (Action, Comedy, 2016)
45		License to Wed (Comedy, Romance, 2007)
45		I Now Pronounce You Chuck & Larry (Comedy, Romance, 2007)
45		The Accidental Husband (Comedy, Romance, 2008)
45		Eagle vs Shark (Comedy, Romance, 2007)
45		Sydney White (Comedy, Romance, 2007)
45		Art School Confidential (Comedy, Drama, 2006)
45		You, Me and Dupree (Comedy, Romance, 2006)
45		Because I Said So (Comedy, Romance, 2007)
45		Knocked Up (Comedy, Romance, 2007)
45		Failure to Launch (Comedy, Romance, 2006)
45		John Tucker Must Die (Comedy, Romance, 2006)
45		Baby Mama (Comedy, Romance, 2008)
45		Yes Man (Comedy, Romance, 2008)
45		My Best Friend's Girl (Comedy, Romance, 2008)
45		The Rules of Attraction (Comedy, Drama, Romance, 2002)
45		Employee of the Month (Comedy, Romance, 2006)
45		The Ex (Comedy, Romance, 2006)
45		Easy Virtue (Comedy, Romance, 2008)
45		Something's Gotta Give (Comedy, Drama, Romance, 2003)
45		What Happens in Vegas (Comedy, Romance, 2008)
45		Priceless (Comedy, Romance, 2006)
45		Van Wilder 2: The Rise of Taj (Comedy, Romance, 2006)
45		The Ten (Comedy, Romance, 2007)
45		The Holiday (Comedy, Romance, 2006)
45		In July (Adventure, Comedy, Romance, 2000)
45		See No Evil, Hear No Evil (Comedy, Crime, 1989)
45		Youth (Comedy, Drama, Music, 2015)
45		Happy Gilmore (Comedy, Sport, 1996)
45		The Big Chill (Comedy, Drama, 1983)
44		Post Grad (Comedy, Romance, 2009)
44		Monsoon Wedding (Comedy, Drama, Romance, 2001)
44		My Life in Ruins (Comedy, Romance, 2009)
44		New in Town (Comedy, Romance, 2009)
44		I Love You, Man (Comedy, Romance, 2009)
44		All About Steve (Comedy, Romance, 2009)
44		I Love You, Beth Cooper (Comedy, Romance, 2009)
44		The Rebound (Comedy, Romance, 2009)
44		She's Out of My League (Comedy, Romance, 2010)
44		The Back-up Plan (Comedy, Romance, 2010)
44		Valentine's Day (Comedy, Romance, 2010)
44		When in Rome (Comedy, Romance, 2010)
44		Leap Year (Comedy, Romance, 2010)
44		L'arnacoeur (Comedy, Romance, 2010)
44		Black Dynamite (Action, Comedy, 2009)
44		Win a Date with Tad Hamilton! (Comedy, Romance, 2004)
44		Guess Who (Comedy, Romance, 2005)
44		Hitch (Comedy, Romance, 2005)
44		Monster-in-Law (Comedy, Romance, 2005)
44		Must Love Dogs (Comedy, Romance, 2005)
44		Taxidermia (Comedy, Drama, Horror, 2006)
44		Just Friends (Comedy, Romance, 2005)
44		The Wedding Date (Comedy, Romance, 2005)
44		Surviving Christmas (Comedy, Romance, 2004)
44		Easy A (Comedy, Romance, 2010)
44		Chasing Liberty (Comedy, Romance, 2004)
44		50 First Dates (Comedy, Romance, 2004)
44		Welcome to Mooseport (Comedy, Romance, 2004)
44		Sleepover (Comedy, Romance, 2004)
44		Laws of Attraction (Comedy, Romance, 2004)
44		Bride Wars (Comedy, Romance, 2009)
44		Miss March (Comedy, Romance, 2009)

Notes: Movies similar to The Heartbreak Kid, Movies like The Heartbreak Kid, Comedy, Romance, Bobby Farrelly, Peter Farrelly, Ben Stiller, Michelle Monaghan, Malin Akerman, Jerry Stiller, Films, Video, Movie Similarities