Most Underrated Comedy Movies of All Time

It’s easy to reel off the greatest comedy films. We know all those movies by heart. But what about the comedies that have fallen under the radar? 

They are the underrated and underappreciated hilarious movies we love as much as the classics, and they deserve just as many rewatches as the big old blockbusters. We’re here to celebrate them. 

Using the one rule of no box office totals over $100 million, here’s a look at the most underrated comedy movies of all time. 

Release date: June 12, 1998

Director: Bob Saget

Starring: Norm Macdonald, Jack Warden, Artie Lange, Don Rickles, Christopher McDonald, Chevy Chase, Traylor Howard

Box office: $10 million

The late Norm Macdonald’s big swing in the movies as a leading man was “Dirty Work” in 1998, based on a short story by “James and the Giant Peach” author Roald Dahl. 

While the movie, directed by Bob Saget, plays more like a string of SNL skits instead of a cogent movie, it’s still hilarious. We also get a great performance by Jack Warden and Artie Lange before drugs ripped apart his career.

Release date: April 18, 2003

Director: John Whitesell

Starring: Jamie Kennedy, Taye Diggs, Anthony Anderson, Blair Underwood, Regina Hall, Bo Derek, Ryan O’Neal

Box office: $34 million

Jamie Kennedy was really having a moment in the early 2000s. He was in big-budget blockbuster movies with the “Scream” franchise and had his own show with “The Jamie Kennedy Experiment,” which ran from 2002 to 2004. 

Right in the middle of it, he even got a shot at being a leading man in his own film and churned out a modest hit with “Malibu’s Most Wanted.” He played Brad “B-Rad” Gluckman, a suburban kid with dreams of being a gangster rapper and whose father is running for governor of California. 

Comedy ensues.