The 10 Most Underrated Comedies of the Past 20 Years

Dirty Work (1998)

"Dirty Work" was very much in line with classic, mid-90's SNL alum-driven comedies such as "Wayne's World," "Billy Madison" and "Tommy Boy." And much like those films, it featured hilarious cameos from the likes of Adam Sandler and Chris Farley (his last film), a bad guy to rival his own Shooter McGavin from "Happy Gilmore" in Christopher McDonald, as well as Chevy Chase's last truly funny performance until...well, probably his last truly funny performance. Yet, sadly, this one has slipped under the radar for years, and it's a damn shame.

Hot Rod (2007)

It's amazing how similar comedies can be, yet how different. Much like "Dirty Work," "Hot Rod" centers on its main character trying to raise money for his father's heart surgery through unconventional methods. However, that's mostly where the similarities stop, as this film centers more on slapstick gags and stunts gone wrong by the man-child protagonist. However, much like "Dirty Work," the entire supporting cast is hilarious and comes together for some laugh-out-loud scenes in this underrated Andy Samberg flick.

Kingpin (1996)

"Kingpin" is every bit as funny as the Farrelly Brothers' most popular comedies "Dumb & Dumber" and "There's Something About Mary," and just so happened to be released right in between them. That was a bit unfortunate for the film, as it has always seemed to be overshadowed by the other two. But don't be fooled; this powerhouse comedy starring the likes of Woody Harrelson, Randy Quaid and the always on his A-game Bill Murray may not only be the Farrelly Brothers' greatest comedic accomplishment, we dare say it rivals "The Big Lebowski" in terms of the greatest bowling comedy of all time.

Starsky & Hutch (2004)

Much like "Kingpin" was to the Farrelly Brothers, "Starsky and Hutch" was Todd Phillips' in-between movie. It came out a year after fan favorite "Old School," and five years before the massively successful "The Hangover" (and yes, we know Phillips directed "School for Scoundrels" prior to "The Hangover" as well, but that film is a stinker). So again, it was another film that seemed to slip through the cracks, even though it also rocked an all-star cast of comedy greats such as Ben Stiller, Owen Wilson and Vince Vaughn in their prime. However, it suffered from people writing it off as poorly adapted bad '70s television, such as the "Dukes of Hazzard," when really it is probably one of Stiller/Wilson/Vaughn's funniest films.

Greenberg (2010)

Speaking of Ben Stiller, the guy can be hit-and-miss in terms of where his acting credits are concerned, but he has never lost his touch, and will surprise you with a tremendously funny performance now and again. "Greenberg" is one such instance. Now, this movie is technically a dramedy, but Stiller, who plays an ex-musician who just got out of the mental hospital from a nervous breakdown, will have you cracking up throughout with his neurotic behavior.

The Cable Guy (1996)

We've already picked two films starring Ben Stiller, so we figured we'd go for the hat trick with "The Cable Guy." This time, however, we have a film that Stiller directed instead. And going by his directorial track record alone we have nothing but great comedies, from "Reality Bites" to "Zoolander" to "Tropic Thunder." Now, people often mistake this film for the one that was the start of Jim Carrey's decline, and that is just flat out absurd. Interesting side note: The title role was originally written for Chris Farley, who had to back out, and was then played by Stiller until he found acting and directing to be too hard to do for this one.

The Ten (2007)

It may have been the more obvious choice to go with the film "Wet Hot American Summer" here, as it was created and starred in by many of the same people. However, over the years, that film has gained such a cult following that a sequel is even going to be produced. So, we figured we should go with "The Ten" instead, which is just as absurdly funny, if not more so. For a film (very, very loosely) based on the Ten Commandments, there is no shortness of raunchy laughs in this one, as well as guest appearances from many now popular actors such as Jason Sudeikis, Rashida Jones and the voice talent of H. Jon Benjamin.

BASEketball (1998)

How could a list of underrated comedies be complete without this gem? "BASEketball" is without a doubt the funniest film centering on a made-up sport. And at that, we'd even be willing to say it's one of the funniest sport movies, period. That is no easy task, until you not only realize that this film stars the geniuses behind "South Park," Trey Parker and Matt Stone, but it was also written by David Zucker, the man responsible for such parody classics as "Airplane!" and "The Naked Gun" films. Sadly, the film has just barely made it's way to cult status, and has still been vastly underwatched.