20. Step Brothers (2008)
If you’ve seen Step Brothers, then you can’t deny that it’s a comedy movie. It definitely kept my attention, but the fact that they (Ferrell and Reilly) were so immature for their age seemed a little weird and unrealistic to me. With that said, I’d still recommend it to those of you who haven’t watched it yet.
19. Anchorman: The Legend of Ron Burgundy (2004)
Will Ferrell and his rambunctious team of co-stars brought us the news in an unconventional manner in this movie that would unequivocally be categorized in the comedy genre.
18. The Hangover (2009)
From the director of “Old School,” The Hangover is a comedy movie that highlighted the fact that some guys just can’t handle Vegas.
17. The 40-Year-Old Virgin (2005)
In his most relatable role of all time, Steve Carell (Over the Hedge) captured the hearts of audiences everywhere with The 40-Year-Old Virgin. Between consistent giggles and snorts, I still find myself involuntary blurting out “THIS” or “I feel attacked” when I go back to re-watch the movie.
16. Bridesmaids (2011)
No caption necessary. If you’ve seen it, you already know the impact it’s had on comedy.
15. Pitch Perfect (2012)
What’s better than six funny women starring in a comedy movie? SEVEN (slightly less funny but more attractive) women starring in a comedy movie. The all-girl, a cappella group made a huge splash in the cinematic waters with this sleeper hit that had the whole family busting out the cups.
14. Wild Hogs (2007)
The star-studded, veteran cast of Tim Allen (The Santa Clause 2, Joe Somebody), William H. Macy (Seabiscuit, Curious George), John Travolta (Hairspray, Urban Cowboy), and Martin Lawrence (Rebound, Open Season) suited up in leather and hit the streets in this cult classic that everyone and their mother has seen at least a few dozen times.
13. Little Man (2006)
For me and many others, the Wayans brothers have cemented themselves as the most hilarious comedy duo of the 21st century. So you can imagine how excited I was when Little Man came out and I got the chance to see Marlon play the role of — you guessed it — a baby!
12. Big Momma’s House (2000)
Martin Lawrence (Welcome Home Roscoe Jenkins) revolutionized comedy movies in a BIG way with this coming-of-age film that had people of all ages begging for air. Lawrence, who is actually a man, disguised himself as a large grandmother for this historic role that helped BMG secure 8 digits at the box office.
11. Drillbit Taylor (2008)
Owen Wilson (Cars, Cars 2, Cars 3) showed his true potential as a live-action comedic talent in this dynamite film that pulled in a whopping $49 million worldwide.
10. Madia’s Family Reunion (2006)
When you think “comedy movies,” the first thing that pops in your head is probably the name “Tyler Perry” or a wacky image of Perry dressed up as an elderly woman. Yep, I’m talking about Madea. The franchise’s most cherished hit, Madea’s Family Reunion, resonated with people of all ages and races and had them chanting for “MORE. MADEA.”
9. From Justin to Kelly (2003)
What happens when the two young stars of the first season of a singing competition television series try out acting for the first time in their lives? 81 minutes of nonstop laughter and fun in a film that’s been billed “the best musical romantic comedy movie based on the show, American Idol”
8. Norbit (2007)
Shrek star Eddie Murphy hit a grand slam with this DreamWorks production, in which he played both a nerdy man and a morbidly obese woman!
7. Kicking & Screaming (2005)
Comedy juggernaut, Will Ferrell outshined all his other roles by starring alongside Robert Duvall (Four Christmases) and Steven Anthony Lawrence (Even Stevens) in this cult classic that sent us all into a fit of laughter. I still feel overwhelmed with nostalgia when I think of all the middle school sleepovers that consisted of me and my friends watching Kicking & Screaming on repeat until 4 a.m.
6. Kangaroo Jack (2003)
Award-winning director, David McNally (Super Bowl XXXIII Budweiser Lobster Commercial) made the world collectively spit out their coffee with one of the highest grossing Australian-American crime comedy live-action/animated films of all time.
5. Daddy Day Camp (2007)
Arguably one of the best comedy actors of the past two decades, Cuba Gooding Jr. (Snow Dogs, Radio) delivered one of his most memorable performances in this monstrous flick that’s jam-packed with shenanigans and antics.
4. Miss Congeniality 2: Armed & Fabulous (2005)
I remember seeing the first Miss Congeniality movie when I was 7-years-old and thinking to myself, “this is the peak of modern cinema.” Five years later, Jesse James’ wife somehow managed to outdo herself in the sequel that put her on the map and solidified herself as an actress.
3. Jack and Jill (2011)
Jack and Jill is what happens when the funniest actor of the late ’90s and early 2000s matures comedically over the course of a decade and gets the zany opportunity to play both a man and woman in the same movie. Adam Sandler (Spanglish) showed the world his true versatility in what’s been dubbed his best performance since Eight Crazy Nights.
2. Disaster Movie (2008)
I’m a huge parody guy so I might be biased with this ranking, but you can’t deny that Disaster Movie was laugh-out-loud-funny from start to finish. With a diverse cast that includes Carmen Electra (Baywatch), Vanessa Minnillo (Total Request Live), and Kim Kardashian (Kim Kardashian Sex Tape with Ray J), it’s hard to miss on a comedy smash hit.
1. Larry the Cable Guy: Health Inspector (2006)
With lines like “I’m gonna go to the bathroom. I gotta take the Browns to the Super Bowl” and “You ever fart so hard your back cracks?” the funniest stand up comedian of the millennium banged out his magnum opus with this feature-length motion picture that pulled in over $15 million at the box office.