Most Underrated Comedy Movies of All Time Some of the greatest comedy films ever made don't get enough credit for being hilarious. And they flew under the radar and still are making us laugh. 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. 30. Dirty Work Twitter / Thatoneguy64 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 Bottom Line: Dirty Work AP Photo 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. 29. Malibu’s Most Wanted Twitter / CrossEyedBear 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 Bottom Line: Malibu’s Most Wanted Peter Kramer / AP Photo 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. 28. Pee-Wee’s Big Adventure Twitter / Lulamaybelle Release date: Aug. 9, 1985 Director: Tim Burton Starring: Paul Reubens, E.G. Daily, Mark Holton, Diane Salinger, Judd Omen Box office: $40.9 million Bottom Line: Pee-Wee’s Big Adventure AP Photo “Pee-Wee’s Big Adventure” made a genius move when it hired Tim Burton as director before he shot to worldwide fame. Not only was Burton’s Pee-wee Herman a hit with audiences, but it also was a hit at the box office, making almost $41 million on a budget of just $7 million. It also spawned two sequels (neither were directed by Burton). Burton’s dark sense of humor and star Paul Reubens’ ability to shoehorn that into his character is what makes this movie tick. And the movie had many ’80s kids doubling over in laughter at it. Fun fact: “Saturday Night Live” legend Phil Hartman was one of the writers for this movie, along with Michael Varhol (who also wrote “The Big Picture” and “The Last Word”) and Reubens. 27. Semi-Pro Twitter / NoDunksInc Release date: Feb. 29, 2008 Director: Kent Alterman Starring: Will Ferrell, Woody Harrelson, Andre 3000, Maura Tierney, Will Arnett, David Koechner, Tim Box office: $43.9 million Bottom Line: Semi-Pro Dan Steinberg / AP Photo Sports movies are hard to pull off — comedy or otherwise — and while “Semi-Pro” was a flop at the box office when it came out, it’s proven rewatchable over the years. “Semi-Pro” nailed the casting and the cool thing for real sports movie aficionados is seeing Woody Harrelson in a follow-up basketball role to “White Men Can’t Jump.” It’s too bad this ended star Will Ferrell’s streak of hit sports spoofs following “Talladega Nights” and “Blades of Glory,” because it’s definitely better than the latter. 26. Bio-Dome Twitter / staticbluebat Release date: Jan. 12, 1996 Director: Jason Bloom Starring: Pauly Shore, Stephen Baldwin, William Atherton, Joey Adams, Kylie Minogue Box office: $13.4 million Bottom Line: Bio-Dome Paul Hurschmann / AP Photo Spew all the hate you want on Pauly Shore’s career. But he was one of the bigger comedy stars in the world in the early to mid-1990s. And no movie had a better concept than “Bio-Dome,” which saw Shore and costar Stephen Baldwin accidentally stuck in an artificial ecological habitat for a year. If Netflix is just tossing cash around, we think a “Bio-Dome” sequel on the cheap would be money well spent. The world would be better for it. Just saying. 25. In a World… Twitter / oldfilmsflicker Release date: Aug. 9, 2013 Director: Lake Bell Starring: Lake Bell, Fred Melamed, Demetri Martin, Ken Marino, Nick Offerman, Tig Notaro, Rob Corddry, Michaela Walkins Box office: $3.1 million Bottom Line: In a World… Danny Moloshok / AP Photo If you haven’t seen “In a World…” yet, it’s still on Hulu as of fall 2021, and you could do a lot less than to spend 90 minutes in the world actress/director Lake Bell created about voice-over artists. Here’s a thought. Bell showed she was very, very good at directing with “In a World…” so maybe studios might check and see if she wants to direct some more. And give her an actual budget. 24. Palm Springs Twitter / benjiballen Release date: July 10, 2020 Director: Max Barbakow Starring: Andy Samberg, Cristin Milloti, Peter Gallagher, J.K. Simmons Box office: N/A Bottom Line: Palm Springs Taylor Jewell / AP Photo There’s nothing about Andy Samberg’s “day in a loop” comedy tour de force that we don’t love, and it would be higher on this list save for the fact that it was released almost exclusively on streaming. What that means is while we think it’s underrated, a lot of that has to do with not getting a real gauge on how many people saw the movie. It seemed like a lot, obviously, but we don’t know for sure. What we do know is Samberg, Cristin Milloti and J.K. Simmons … that works. 23. Black Sheep Twitter / MShoneBahar Release date: Feb. 2, 1996 Director: Penelope Spheeris Starring: Chris Farley, David Spade, Tim Matheson, Christine Ebersole, Gary Busey Box office: $32.4 million Bottom Line: Black Sheep Richard Drew / AP Photo We didn’t get to see nearly enough of Chris Farley’s talents before he died of a drug overdose in 1997 at the age of 33. It’s widely thought that his only truly great comedy was “Tommy Boy.” Which would be right. But he does have a similar and suitable companion to his centerpiece film with “Black Sheep,” and it’s also with the same costar, David Spade. This comedy has been wrongfully pilloried over the years. Yes, Farley’s playing almost the exact same character in both movies. So what? He’s hilarious. And so’s the film. 22. Hot Tub Time Machine Twitter / SpacewomanR Release date: March 26, 2010 Director: Steve Pink Starring: John Cusack, Rob Corddry, Craig Robinson, Clark Duke, Crisping Glover, Lizzy Caplan, Chevy Chase Box office: $64.6 million Bottom Line: Hot Tub Time Machine Katy Winn / AP Photo John Cusack spent long enough in “serious” movies that it was a welcome sight to see him getting back in the comedy game (where his career first started) with “Hot Tub Time Machine” in 2010. We love a good time travel movie, and as far as comedies go, this is one of the best to blend the two genres together. Cusack showed he was as good at knowing when to get back in the comedy game as when to get out. He was the only member of the main cast to not appear in the 2015 sequel, which grossed almost $50 million less than the original and was demolished by critics and moviegoers. 21. How High Twitter / daaglue Release date: Dec. 21, 2001 Director: Jesse Dylan Starring: Method Man, Redman, Obba Babatnde, Mike Epps, Jeffrey Jones, Fred Willard, Lark Voorhies Box office: $31.3 million Bottom Line: How High John Davisson / AP Photo As far as stoner comedies go, you could do way worse than “How High” starring two of the greatest rappers to ever live at the peak of their careers. Here’s a slight glimpse into the madness. Method Man and Redman smoke a blunt together that contains a marijuana strain partially grown with the ashes of a dead friend right before taking the SATs. Their dead friend appears to them as a ghost during the test and guides them to perfect scores that get them into Harvard. And that’s just the first 10 minutes. 20. The Distinguished Gentleman Twitter / framefound Release date: Dec. 4, 1992 Director: Jonathan Lynn Starring: Eddie Murphy, Lane Smith, Sheryl Lee Ralph, Joe Don Baker, Victoria Rowell, Charles Dutton, Kevin McCarthy, James Garner Box office: $82.3 million Bottom Line: The Distinguished Gentleman Jose Goitia / AP Photo Eddie Murphy had one of the more underrated movie star years of all time in 1992, putting out two huge hits with “Boomerang” and “The Distinguished Gentleman” back-to-back. Murphy wasn’t the only one associated with “Gentleman” who had a pair of hits in 1992. Director Jonathan Lynn also had the Oscar-winning “My Cousin Vinny” come out in the same year. 19. Dick Twitter / filmgal Release date: Aug. 4, 1999 Director: Andrew Fleming Starring: Kirsten Dunst, Michelle Williams, Dan Hedaya, Harry Shearer, Dave Foley, Will Ferrell, Saul Rubinek, Bruce McCulloch Box office: $6.3 million Bottom Line: Dick Chris Pizzello / AP Photo This is the rare historical fiction comedy. In this case, two future mega-stars in Kirsten Dunst and Michelle Williams (what great casting) play teenage girls who unwittingly bust open the Watergate scandal. There have been a lot of great movies made about Watergate and Richard Nixon, but there’s only really truly funny one. And this is it. And there are few better portrayals of Nixon than Dan Hedaya’s. 19. BASEketball Twitter / DillonZulkowski Release date: July 31, 1998 Director: David Zucker Starring: Trey Parker, Matt Stone, Yasmine Bleeth, Jenny McCarthy, Robert Vaughn, Ernest Borgnine Box office: $7 million Bottom Line: BASEketball Damian Dovarganes / AP Photo The Comedy Central cartoon series “South Park” was becoming so popular in the late 1990s and early 2000s that the show’s two creators, Trey Parker and Matt Stone, were getting movies greenlit starring themselves. “BASEketball” was the most noticeable of those — and the biggest flop when it hit theaters in 1998, making just $7 million at the box office against its almost $25 million budget. The movie was seemingly ahead of its time in its critiques of professional sports. Maybe it came out about 20 years too soon? 17. Three Amigos Twitter / RetroNewsNow Release date: Dec. 12, 1986 Director: John Landis Starring: Steve Martin, Chevy Chase, Martin Short, Alfonso Arau, Tony Plana, Patrice Martinez Box office: $39.2 million Bottom Line: Three Amigos Frankie Ziths / AP Photo As you can probably imagine, expectations were sky-high for the pairing of three of the greatest comedians of all time with one of the greatest comedic directors of all time in John Landis. With that, “Three Amigos” was such a resounding thud when it came out that it did damage to all their careers. Over the years, we’ve given it much more credit as a piece of comedic nostalgia. And it’s much funnier in 2021 than it was in 1986, somehow. 16. Welcome Home, Roscoe Jenkins Twitter / NetflixFilm Release date: Feb. 8, 2008 Director: Malcolm D. Lee Starring: Martin Lawrence, Joy Bryant, Louis C.K., Michael Clarke Duncan, Mike Epps, Mo’Nique, Nicole Ari Parker, Cedric the Entertainer, James Earl Jones, Margaret Avery Box office: $43.6 million Bottom Line: Welcome Home, Roscoe Jenkins Evan Agostini / AP Photo Martin Lawrence has been in some blockbuster films, but he hasn’t been in a lot of truly great ones. “Welcome Home, Roscoe Jenkins” comes close in terms of comedy. Lawrence may have been in his prime in the early 2000s, but we got to see him pitch one more no-hitter with this movie, even if it didn’t make a ton of money. There’s something great about the “coming home” type of movie that this perfects. 15. I Love You, Man Twitter / kaylalcurry Release date: March 20, 2009 Director: John Hamburg Starring: Paul Rudd, Jason Segel, Rashida Jones, Andy Samberg, J.K. Simmons, Jane Curtin, Jon Favreau, Jaime Pressly, Lou Ferrigno Box office: $92.3 million Bottom Line: I Love You, Man Evan Agostini / AP Photo Jason Segel’s forays into films and television have been few and far between in the last few years, but we have movies like “I Love You, Man” to go by as a testament to his talent. He and Paul Rudd’s chemistry is off the charts. Like any great comedy, “I Love You, Man” is only as good as its supporting roles, and the cast here is amazing, led by Rashida Jones as Rudd’s fiance. 14. Best in Show Twitter / framefound Release date: Feb. 29, 2000 Director: Christopher Guest Starring: Jennifer Coolidge, Christopher Guest, John Michael Higgins, Eugene Levy, Jane Lynch, Michael McKean, Catherine O’Hara, Parker Posey, Fred Willard Box office: $20.8 million Bottom Line: Best in Show AP Photo We could have put a gaggle of Christopher Guest’s films on this list, but we we went with “Best in Show” and hesitated to do that because it’s so beloved. Just consider this our Oscar-esque lifetime achievement award for one of the most underrated comedic filmmakers of all time. “Schitt’s Creek” fans will see the thread of humor from that show in this movie. “Best in Show” is cowritten by “Schitt’s” star Eugene Levy. 13. Next Friday Twitter / StessTheEmcee Release date: Jan. 12, 2000 Director: Steve Carr Starring: Ice Cube, Mike Epps, John Witherspoon, Tamala Jones, Zeus “Tiny” Lister, Justin Pierce, Jacob Vargas, Lisa Rodriguez Box office: $59.8 million Bottom Line: Next Friday Twitter / framefound Chris Tucker didn’t want to come back for the “Friday” sequel after he said he was never paid for the original. Mike Epps did an above-average job of filling in for Tucker, and the sequel was also a hit. It was also really funny, thanks in no small part to the addition of talented newcomers like Epps, Jacob Vargas and “Kids” star Justin Pierce, who committed suicide just months after the movie’s release. 12. My Blue Heaven Twitter / billthader Release date: Aug. 17, 1990 Director: Herbert Ross Starring: Steve Martin, Rick Moranis, Joan Cusack, Carol Kane Box office: $23.6 million Bottom Line: My Blue Heaven Twitter / framefound You can blow your gangster movie-loving friends’ minds when you drop this fact on them. The main characters in “Goodfellas” and “My Blue Heaven” were both based on the same real-life person, mafia snitch Henry Hill. Here’s another fact that will blow your mind. “Goodfellas” was based on the book “Wiseguy” by Nicholas Pileggi, and “My Blue Heaven” was written by Pileggi’s wife, legendary writer/director Nora Ephron. Fuhgeddaboudit. 11. Role Models Twitter / SciFi31 Release date: Nov. 7, 2008 Director: David Wain Starring: Sean William Scott, Paul Rudd, Christopher Mintz-Plasse, Bobb’e J. Thompson, Jane Lynch, Elizabeth Banks, Ken Marino Box office: $92.4 million Bottom Line: Role Models Jason Decrow / AP Photo This is one of several appearances by pre-Marvel Paul Rudd on this list. While his pairing with Sean William Scott helps make “Role Models” tick, this movie really belongs to its two younger stars — post-“Superbad” Christopher Mintz-Plasse and Bobb’e J. Thompson. And it’s Thompson who gets to deliver the movie’s signature line: “You white, you Ben Affleck.” 10. Back to School Twitter / skunkgod1 Release date: June 13, 1986 Director: Alan Metter Starring: Rodney Dangerfield, Keith Gordon, Burt Young, Robert Downey Jr., William Zabka, Sally Kellerman, Adrienne Barbeau, Sam Kinison, Ned Beatty Box office: $91.3 million Bottom Line: Back to School AP Photo When you hear someone mention the “Triple Lindy,” it’s a beacon signaling out to all other “Back to School” fans to come together and sing the praises of the late Rodney Dangerfield and his apex moment — a comedy that grossed roughly $227 million at the box office in today’s money. There is so much to love about “Back to School” outside of Dangerfield’s comedy tour de force, but we want to give a couple of special shoutouts to William Zabka as the perfect 1980s bad guy, Robert Downey Jr. as the zoned-out college roomie and Kurt Vonnegut for making an out-of-nowhere cameo. If you haven’t seen “Back to School,” check it out. If you have seen it, now would be a good time for a rewatch. 9. Always Be My Maybe Twitter / raveinspades Release date: May 31, 2019 Director: Nahnatchka Khan Starring: Ali Wong, Randall Park, James Saito, Michelle Buteau, Vivian Bang, Daniel Dae Kim, Keanu Reeves Box office: N/A Bottom Line: Always Be My Maybe Mark Von Holden / AP Photo Streaming movies are pretty tough to gauge, but we wanted to make sure to include “Always Be My Maybe” because in an era when streaming movies seem to proliferate, this one stands out and shouldn’t be forgotten. Director Nahnatchka Khan may have made her film directorial debut with “Always,” but she’s been in the game for a long time. She was a television writer and director for over 20 years before Netflix tossed some cash her way. The electric chemistry between Ali Wong and Randall Park (and, of course, Keanu Reeves) did the rest. 8. The Foot Fist Way Twitter / FunnyFOOOLS Release date: May 30, 2008 Director: Jody Hill Starring: Danny McBride, Ben Best Box office: $245,000 Bottom Line: The Foot Fist Way Matt Sayles / AP Photo We don’t have Danny McBride without “The Foot Fist Way” — a low-budget movie about a pathetic taekwondo instructor that was released in January 2006 but didn’t begin to catch hold with audiences until it came out on DVD in 2008. One of the crazier twists about “The Foot Fist Way” was when a then-unknown McBride appeared in character on “The Conan O’Brien Show” in 2008 and audiences were aghast at how terrible his taekwondo demonstration went. The movie included another underrated comic legend, the late Ben Best, who later cocreated “Eastbound & Down” with McBride and “The Foot Fist Way” director Jody Hill. 7. Real Genius Twitter / LoLuVal Release date: Aug. 7, 1985 Director: Martha Coolidge Starring: Val Kilmer, Gabe Jarret, Michelle Meyrink, William Atherton, Robert Prescott, Jon Gries, Dean Devlin, Yuji Okumoto Box office: $13 million Bottom Line: Real Genius AP Photo Getting an up-and-coming Val Kilmer in a perfect role, in his youth, was amazing casting by the folks behind “Real Genius.” The real star of this incredibly rewatchable college/techie comedy is director Martha Coolidge, who had an amazing three-film run with “Valley Girl,” “Real Genius,” and “Rambling Rose,” which earned two Oscar nominations. Coolidge’s career after the early 1990s was a much different story, with miss after miss in movies she directed until she essentially turned into almost a solely high-profile television director over the last two decades. 6. Waiting… Twitter / _amandagrant_ Release date: Oct. 17, 2005 Director: Rob McKittrick Starring: Ryan Reynolds, Anna Faris, Justin Long, David Koechner, John Francis Daley, Chi McBride, Luis Guzman, Kaitlin Doubleday, Alanna Ubachm, Andy Milonakis Box office: $18.6 million Bottom Line: Waiting… Louis Lanzano / AP Photo Almost anyone who has ever worked in a restaurant knows this movie chapter and verse. What makes “Waiting…” great is its brilliant casting led by Ryan Reynolds, Anna Faris, Chi McBride and Luis Guzman. Waiting in the wings as one of the supporting characters is John Francis Daley, the “new hire” who steals the show in the end. Daley’s talents aren’t just in acting. He’s also the screenwriter behind “Spider-Man: Homecoming” and “Horrible Bosses” and is the writer/director behind the upcoming big-budget version of “Dungeons & Dragons” starring Chris Pine and Michelle Rodriguez. 5. I’m Gonna Git You Sucka Twitter / 80sMontagePod Release date: Jan. 11, 1989 Director: Keenen Ivory Wayans Starring: Keenen Ivory Wayans, Bernie Casey, Antonio Fargas, Isaac Hayes, Jim Brown, Janet Dubois Box office: $13 million Bottom Line: I’m Gonna Git You Sucka Kevork Djansezian / AP Photo In the history of parody films, you can’t do much better than Keenen Ivory Wayans’ “I’m Gonna Git You Sucka.” It’s a parody of Arnold Schwarzenegger and Sylvester Stallone movies and the springboard to Ivory Wayans’ groundbreaking television series “In Living Color” and the entire Wayans empire. The film’s premise is as ridiculous as any you will ever hear. Decorated soldier Jack Slade (Wayans) returns home to Any Ghetto, USA, after learning his younger brother died of an “OG” … better known as an overdosing on gold chains. Slade then brings together former Black heroes to help him get revenge on Mr. Big. 4. Super Troopers Twitter / charlesthorp Release date: Feb. 15, 2002 Director: Jay Chandrasekhar Starring: Jay Chandrasekhar, Kevin Heffernan, Steve Lemme, Paul Soter, Brian Cox, Daniel von Bargen, Marisa Coughlan Box office: $23.2 million Bottom Line: Super Troopers Richard Shotwell / AP Photo This off-brand stoner comedy focusing on incompetent Vermont state troopers is perfect for your late-night viewing needs. And, yes, that really is award-winning actor Brian Cox as the commander. One amazing financial statistic about “Super Troopers” is that while the movie made $23 million at the box office on a budget of around $2 million, it reportedly made another $71 million off rentals and sales since its release. 3. Grandma’s Boy Twitter / Sheena_65532` Release date: Jan. 6, 2006 Director: Nicholaus Goosen Starring: Allen Covert, Linda Cardellini, Doris Roberts, Nick Swardson, Peter Dante, Shirley Jones, Shirley Knight, Joel David Moore, Kevin Nealon Box office: $6.6 million Bottom Line: Grandma’s Boy Shea Walsh / AP Photo Fans of Adam Sandler movies know that he keeps essentially the same group of actors (and friends) in supporting roles in his movies over the years. “Grandma’s Boy” was their shot to do it on their own. Allen Covert — Sandler’s limo driver friend from “The Wedding Singer” — is perfect as the slacker video-game creator in the lead. But the cast’s chemistry is what gives this movie such staying power. And it’s been a cable and streaming staple for over a decade now. 2. Money Talks Twitter / iamcalel Release date: Aug. 22, 1997 Director: Brett Ratner Starring: Chris Tucker, Charlie Sheen, Heather Locklear, Paul Sorvino, Elise Neal Box office: $48.4 million Bottom Line: Money Talks Twitter / JackieChanIsThe Watching Chris Tucker perform on the big screen in the mid-to-late 1990s was getting to see something truly special. It was like watching Michael Jordan in his prime. “Money Talks” got Tucker across from some decent talent and let him shine, as post-prime Charlie Sheen got out of his way just enough. For the very best moments in the movie, look no further than Tucker’s scenes with Paul Sorvino. They are hilarious. This movie is also a testament to what could have been. Tucker made precious few films in his prime. For example, he had three movies come out in 1997, then just three films over the next decade and all in the “Rush Hour” franchise. 1. Booksmart Twitter / Variety Release date: May 24, 2019 Director: Olivia Wilde Starring: Beanie Feldstein, Kaitlyn Dever, Jessica Williams, Lisa Kudrow, Jason Sudeikies Box office: $25 million Bottom Line: Booksmart Jack Plunkett / AP Photo It’s a shame director Olivia Wilde’s “Booksmart” fell flat at the box office in 2019, making just $25 million, because the legacy of the film seems to show it’s going to live far beyond whatever numbers it brought in during its theatrical release. The two stars of the movie — Kaitlyn Dever and Beanie Feldstein — have shown they’re two of the best young actors in the world with other projects since the movie’s release. And the movie itself isn’t just hilarious. It’s hilarious and infinitely rewatchable. Feldstein was actually nominated for a Golden Globe for her role.
