99		American Pie (Comedy, 1999)
99		Fast Times at Ridgemont High (Comedy, Drama, 1982)
99		Friends with Benefits (Comedy, Romance, 2011)
99		YPF (Comedy, Drama, Romance, 2007)
99		Knocked Up (Comedy, Romance, 2007)
99		Love & Other Drugs (Comedy, Drama, Romance, 2010)
95		Sixteen Candles (Comedy, Romance, 1984)
94		American Wedding (Comedy, Romance, 2003)
92		The Girl Next Door (Comedy, Drama, Romance, 2004)
91		Sex Drive (Adventure, Comedy, Romance, 2008)
90		Just Friends (Comedy, Romance, 2005)
89		Miss Pettigrew Lives for a Day (Comedy, Romance, 2008)
87		The Last Kiss (Comedy, Drama, Romance, 2006)
87		Les poupées russes (Comedy, Drama, Romance, 2005)
85		Love and Other Disasters (Comedy, Romance, 2006)
83		Someone Like You... (Comedy, Romance, 2001)
82		American Reunion (Comedy, 2012)
82		Weird Science (Comedy, Romance, Sci-Fi, 1985)
82		Factotum (Comedy, Drama, Romance, 2005)
80		Clerks II (Comedy, 2006)
79		The Hangover (Comedy, 2009)
78		American Pie 2 (Comedy, 2001)
77		Alfie (Comedy, Drama, Romance, 2004)
76		Love, Rosie (Comedy, Romance, 2014)
76		The Wackness (Comedy, Drama, Romance, 2008)
75		EuroTrip (Comedy, 2004)
75		Mallrats (Comedy, Romance, 1995)
75		Bachelor Party (Comedy, 1984)
74		Alex & Emma (Comedy, Romance, 2003)
73		Confessions of a Dangerous Mind (Biography, Comedy, Crime, 2002)
72		The Dictator (Comedy, Romance, 2012)
72		Wild at Heart (Comedy, Crime, Romance, 1990)
72		What's Your Number? (Comedy, Romance, 2011)
72		Working Girl (Comedy, Drama, Romance, 1988)
72		Cashback (Comedy, Drama, Romance, 2006)
71		In the Land of Women (Comedy, Drama, Romance, 2007)
70		Terms of Endearment (Comedy, Drama, 1983)
70		Revenge of the Nerds (Comedy, 1984)
70		Valley Girl (Comedy, Romance, 1983)
70		The Wedding Date (Comedy, Romance, 2005)
70		Adventureland (Comedy, Drama, Romance, 2009)
69		As Good as It Gets (Comedy, Drama, Romance, 1997)
69		Varsity Blues (Comedy, Drama, Romance, 1999)
69		Sideways (Adventure, Comedy, Drama, 2004)
69		Down with Love (Comedy, Romance, 2003)
68		Office Space (Comedy, 1999)
68		Don Jon (Comedy, Drama, Romance, 2013)
68		Wet Hot American Summer (Comedy, Romance, 2001)
67		Imagine Me & You (Comedy, Drama, Romance, 2005)
67		Married to the Mob (Comedy, Crime, Romance, 1988)
67		Venus (Comedy, Drama, Romance, 2006)
67		Birthday Girl (Comedy, Crime, Thriller, 2001)
66		Uptown Girls (Comedy, Drama, Romance, 2003)
66		The Rules of Attraction (Comedy, Drama, Romance, 2002)
65		Date Night (Comedy, Crime, Romance, 2010)
64		Two Weeks Notice (Comedy, Romance, 2002)
64		Easy Virtue (Comedy, Romance, 2008)
64		Anger Management (Comedy, 2003)
63		Almost Famous (Adventure, Comedy, Drama, 2000)
63		Get Him to the Greek (Comedy, Music, 2010)
63		L'arnacoeur (Comedy, Romance, 2010)
62		Jersey Girl (Comedy, Drama, Romance, 2004)
62		Elizabethtown (Comedy, Drama, Romance, 2005)
62		This Is 40 (Comedy, Romance, 2012)
62		Human Nature (Comedy, Drama, Mystery, 2001)
62		The Man with Two Brains (Comedy, Romance, Sci-Fi, 1983)
61		The Jane Austen Book Club (Comedy, Drama, Romance, 2007)
61		The Sessions (Biography, Comedy, Drama, 2012)
61		In the Company of Men (Comedy, Drama, 1997)
61		Living in Oblivion (Comedy, Drama, 1995)
60		Sleepover (Comedy, Romance, 2004)
60		Art School Confidential (Comedy, Drama, 2006)
60		The Private Lives of Pippa Lee (Comedy, Drama, Romance, 2009)
60		Wedding Crashers (Comedy, Romance, 2005)
60		Monster-in-Law (Comedy, Romance, 2005)
59		Roger Dodger (Comedy, Drama, 2002)
59		Role Models (Comedy, 2008)
59		Empire Records (Comedy, Drama, Music, 1995)
59		To Die For (Comedy, Crime, Drama, 1995)
58		One Night at McCool's (Comedy, Crime, 2001)
58		Serendipity (Comedy, Romance, 2001)
58		America's Sweethearts (Comedy, Romance, 2001)
58		The Whole Nine Yards (Comedy, Crime, 2000)
58		Get Smart (Action, Adventure, Comedy, 2008)
57		Just Like Heaven (Comedy, Fantasy, Romance, 2005)
57		Dev.D (Comedy, Drama, Romance, 2009)
57		A Good Year (Comedy, Drama, Romance, 2006)
57		Three to Tango (Comedy, Romance, 1999)
57		Bewitched (Comedy, Fantasy, Romance, 2005)
57		Shall We Dance (Comedy, Drama, Romance, 2004)
57		Super Troopers (Comedy, Crime, Mystery, 2001)
56		Barton Fink (Comedy, Drama, 1991)
56		Punch-Drunk Love (Comedy, Drama, Romance, 2002)
56		The Truth About Cats & Dogs (Comedy, Romance, 1996)
56		L'auberge espagnole (Comedy, Drama, Romance, 2002)
56		This Is the End (Comedy, Fantasy, 2013)
56		Short Cuts (Comedy, Drama, 1993)
56		Chaos Theory (Comedy, Drama, Romance, 2008)
56		Buffalo '66 (Comedy, Crime, Drama, 1998)
56		Laggies (Comedy, Romance, 2014)
55		Saved! (Comedy, Drama, 2004)
55		The Door in the Floor (Comedy, Drama, 2004)
55		The Kids Are All Right (Comedy, Drama, Romance, 2010)
55		It's Complicated (Comedy, Drama, Romance, 2009)
55		Silver Linings Playbook (Comedy, Drama, Romance, 2012)
55		Heartbreakers (Comedy, Crime, Romance, 2001)
55		The World According to Garp (Comedy, Drama, 1982)
54		The Ten (Comedy, Romance, 2007)
54		Igby Goes Down (Comedy, Drama, 2002)
54		Something Borrowed (Comedy, Drama, Romance, 2011)
54		But I'm a Cheerleader (Comedy, Drama, Romance, 1999)
54		The Ice Harvest (Comedy, Crime, Drama, 2005)
54		Aquamarine (Comedy, Family, Fantasy, 2006)
54		Kick-Ass (Action, Comedy, 2010)
53		I Love You, Man (Comedy, Romance, 2009)
53		Picture Perfect (Comedy, Drama, Romance, 1997)
53		Due Date (Comedy, Drama, 2010)
53		28 Days (Comedy, Drama, 2000)
53		The Joneses (Comedy, Drama, 2009)
53		Casse-tête chinois (Comedy, Drama, Romance, 2013)
53		Happiness (Comedy, Drama, 1998)
52		Wimbledon (Comedy, Romance, Sport, 2004)
52		Love Wrecked (Adventure, Comedy, Romance, 2005)
52		Human Traffic (Comedy, Music, 1999)
52		Project X (Comedy, Crime, 2012)
52		In Her Shoes (Comedy, Drama, Romance, 2005)
52		The Three Stooges (Comedy, 2012)
52		Bull Durham (Comedy, Romance, Sport, 1988)
52		Ted (Comedy, Fantasy, 2012)
52		The Wolf of Wall Street (Biography, Comedy, Crime, 2013)
52		Dil Chahta Hai (Comedy, Drama, Romance, 2001)
52		Think Like a Man (Comedy, Romance, 2012)
51		Music and Lyrics (Comedy, Music, Romance, 2007)
51		About a Boy (Comedy, Drama, Romance, 2002)
51		The Importance of Being Earnest (Comedy, Drama, Romance, 2002)
51		The Other Woman (Comedy, Romance, 2014)
51		Man on the Moon (Biography, Comedy, Drama, 1999)
51		What If (Comedy, Romance, 2013)
51		Wake Up Sid (Comedy, Drama, Romance, 2009)
51		Bean (Comedy, Family, 1997)
51		You Kill Me (Comedy, Crime, Romance, 2007)
51		Withnail & I (Comedy, Drama, 1987)
50		I Heart Huckabees (Comedy, 2004)
50		Clueless (Comedy, Romance, 1995)
50		Solitary Man (Comedy, Drama, Romance, 2009)
50		The Overnight (Comedy, Mystery, 2015)
50		Kate & Leopold (Comedy, Fantasy, Romance, 2001)
50		Everybody Wants Some!! (Comedy, 2016)
50		See No Evil, Hear No Evil (Comedy, Crime, 1989)
50		Overboard (Comedy, Romance, 1987)
50		Hot Shots! Part Deux (Action, Comedy, 1993)
50		Basket Case (Comedy, Horror, 1982)
50		Filth (Comedy, Crime, Drama, 2013)
49		Cool World (Animation, Comedy, Fantasy, 1992)
49		The Wedding Singer (Comedy, Music, Romance, 1998)
49		Mansfield Park (Comedy, Drama, Romance, 1999)
49		Drop Dead Gorgeous (Comedy, Romance, Thriller, 1999)
49		Never Been Kissed (Comedy, Drama, Romance, 1999)
49		Juno (Comedy, Drama, 2007)
49		200 Cigarettes (Comedy, Drama, Romance, 1999)
48		New in Town (Comedy, Romance, 2009)
48		Grind (Adventure, Comedy, Sport, 2003)
48		Chasing Amy (Comedy, Drama, Romance, 1997)
48		Loser (Comedy, Romance, 2000)
48		Another Year (Comedy, Drama, 2010)
47		Jab We Met (Comedy, Drama, Romance, 2007)
47		Green Card (Comedy, Drama, Romance, 1990)
47		Jennifer's Body (Comedy, Fantasy, Horror, 2009)
47		I Love You Phillip Morris (Biography, Comedy, Crime, 2009)
47		My Sassy Girl (Comedy, Drama, Romance, 2001)
47		Man Up (Comedy, Drama, Romance, 2015)
47		Mermaids (Comedy, Drama, Romance, 1990)
47		Tootsie (Comedy, Drama, Romance, 1982)
47		Cry-Baby (Comedy, Musical, Romance, 1990)
47		The Princess Diaries 2: Royal Engagement (Comedy, Family, Romance, 2004)
47		Horrible Bosses (Comedy, Crime, 2011)
47		Riding in Cars with Boys (Biography, Comedy, Drama, 2001)
47		The Mexican (Adventure, Comedy, Crime, 2001)
47		A Very Harold & Kumar 3D Christmas (Adventure, Comedy, 2011)
47		Mannequin (Comedy, Fantasy, Romance, 1987)
47		Conversations with Other Women (Comedy, Drama, Romance, 2005)
46		In July (Adventure, Comedy, Romance, 2000)
46		Don't Be a Menace to South Central While Drinking Your Juice in the Hood (Comedy, Crime, 1996)
46		This Is Where I Leave You (Comedy, Drama, 2014)
46		No Reservations (Comedy, Drama, Romance, 2007)
46		Rory O'Shea Was Here (Comedy, Drama, 2004)
46		Zero Effect (Comedy, Crime, Drama, 1998)
46		Happy Gilmore (Comedy, Sport, 1996)
46		Obvious Child (Comedy, Drama, 2014)
46		Let's Be Cops (Comedy, 2014)
45		Laws of Attraction (Comedy, Romance, 2004)
45		Must Love Dogs (Comedy, Romance, 2005)
45		Win a Date with Tad Hamilton! (Comedy, Romance, 2004)
45		Meet the Fockers (Comedy, Romance, 2004)
45		The Ex (Comedy, Romance, 2006)
45		Victor Victoria (Comedy, Music, Musical, 1982)
45		How Do You Know (Comedy, Drama, Romance, 2010)
45		An American Werewolf in Paris (Comedy, Fantasy, Horror, 1997)
45		Guess Who (Comedy, Romance, 2005)
45		You, Me and Dupree (Comedy, Romance, 2006)
45		Hitch (Comedy, Romance, 2005)
45		50 First Dates (Comedy, Romance, 2004)
45		Van Wilder 2: The Rise of Taj (Comedy, Romance, 2006)
45		Welcome to Mooseport (Comedy, Romance, 2004)
45		Addams Family Values (Comedy, Fantasy, 1993)
45		50/50 (Comedy, Drama, Romance, 2011)
45		Team America: World Police (Action, Comedy, 2004)
45		Chasing Liberty (Comedy, Romance, 2004)
45		Surviving Christmas (Comedy, Romance, 2004)
45		Failure to Launch (Comedy, Romance, 2006)
45		Tamara Drewe (Comedy, Drama, Romance, 2010)
45		Joe Versus the Volcano (Comedy, Romance, 1990)
45		John Tucker Must Die (Comedy, Romance, 2006)
45		Four Rooms (Comedy, 1995)
45		Arthur (Comedy, Romance, 1981)
45		Wedding Daze (Comedy, Romance, 2006)
45		Postcards from the Edge (Comedy, Drama, 1990)
45		Roxanne (Comedy, Romance, 1987)
45		Where the Heart Is (Comedy, Drama, Romance, 2000)
45		Priceless (Comedy, Romance, 2006)
45		Employee of the Month (Comedy, Romance, 2006)
45		Along Came Polly (Comedy, Romance, 2004)
45		The Holiday (Comedy, Romance, 2006)

Notes: Movies similar to The 40-Year-Old Virgin, Movies like The 40-Year-Old Virgin, Comedy, Romance, Judd Apatow, Steve Carell, Catherine Keener, Paul Rudd, Romany Malco, Films, Video, Movie Similarities