No one could have expected that Clerks, filmed at the convenience and video stores at which Smith worked in real life, would still be influencing writers a quarter-century later. Made for almost nothing, it was a huge hit around the world, thanks mostly to Sandler’s fearless comedy style and his excellent chemistry with Drew Barrymore as the waitress who wins over the wedding singer’s heart. Bill & Ted’s Excellent Adventure. Crystal stars as an average guy who channels his mid-life crisis into a week on a cattle drive with two of his best buddies, played by Daniel Stern and Bruno Kirby. HBO Max has the classic original, the one that stars Zero Mostel and Gene Wilder as a pair of producers who try to make the biggest flop they can … and fail. (The sequel, Be Cool, is also on HBO Max.)

Happy Gilmore

Netflix may have all those new Adam Sandler comedies, but HBO Max has the classics. This Is Spinal Tap

All mockumentaries owe a massive debt to Rob Reiner’s 1984 directorial debut. Rene Russo plays the romantic interest in this one while Don Johnson and Cheech Marin have major supporting roles. It’s a perfectly calibrated comedy with phenomenal performances all around, including Rene Russo, Danny DeVito, Delroy Lindo, and Gene Hackman. *Dave

Ivan Reitman directed a script by Gary Ross that gave the great Kevin Kline one of his best comedic roles. Reuniting with most of his favorite colleagues and friends after the success of Waiting for Guffman, which is also on HBO Max, Guest and his ensemble dropped what is quite simply one of the best comedies ever made. The film features fantastic work from Paul Giamatti, Hope Davis, Judah Friedlander, and James Urbaniak, who plays the inimitable Robert Crumb. It really defined his man-child persona, one that he’s still working to this day. It’s a delightful comedy about a memorable oddball. The wonderful Richard E. Best in Show

Movies don’t get funnier than Christopher Guest’s brilliant mockumentary about people obsessed with their canine counterparts. Photo: Orion Pictures

This article is updated frequently as titles leave and enter HBO and HBO Max. Gene Kelly, Debbie Reynolds, and Donald O’Connor are as charming as charming can be, and the movie contains some of the best choreography of its era, and not just in the titular number. Metropolitan

Whit Stillman made his directorial and screenwriting debut with this clever 1990 film about a group of rich kids in Manhattan. It’s joyous from front to back. Clerks

Kevin Smith rocked the indie-filmmaking world with a comedy that was shot for almost nothing and became a worldwide hit. American Splendor

Shari Springer Berman and Robert Pulcini wrote and directed the 2003 biopic that’s as strange as its subject: the one and only Harvey Pekar. *Jerry Maguire

One of Cameron Crowe’s best films became something of a punchline with its heavily quoted lines (“Show me the money,” “You had me at hello,” everything that cute kid says), but it’s still a wonderful romantic comedy that has held up incredibly well in the quarter-century since its release. Pick your favorites, and then come back here for more. Bowfinger

One of Eddie Murphy’s top performances is in this 1999 satire from the great Frank Oz. Chan’s incredible action skills are balanced perfectly by Tucker’s rapid-fire comedy delivery. All recommendations are made independently by our editors. Everyone could see a little of these two nihilists in themselves. *Tin Cup

The great Ron Shelton reunited with his Bull Durham star in a 1996 sports comedy that moved the premise from baseball to golf but once again hinged on the undeniable screen charisma of Kevin Costner. The reason these movies work is Myers’s complete fearlessness — he’ll do anything to make you laugh. The actor plays Rob Gordon, a Chicago music store owner who struggles with relationships and responsibility. Dumb & Dumber

There was a time when Jim Carrey was arguably the biggest star in the world, and this movie, coming on the heels of Ace Ventura and The Mask, was really the peak of that fame. Down and Out in Beverly Hills

Richard Dreyfuss and Bette Midler are perfect in this ’80s classic as a pair of rich socialites whose life is turned upside down when they save the life of a suicidal homeless man, played by a perfectly cast Nick Nolte. There’s a little bit of something for anyone looking for something to make them laugh, from silent classics to recent hits. Those people were wrong. The first movie is still the best, but HBO Max has all three if you’re in the mood for a marathon. City Slickers

Billy Crystal was at the peak of his fame here. Don’t have HBO Max yet? City Lights

Charlie Chaplin helped define comedy in his string of major motion pictures, and City Lights is one of his most beloved works, a romantic comedy that centers Chaplin’s Tramp character in a love story with a blind girl and a friendship with an alcoholic millionaire. It’s clever in ways that would redefine comedy, and it’s still influencing the genre. The drama leading up to the release of The Interview, a movie that made Kim Jong-un so mad that he ordered a hack of Sony and threatened terrorist attacks against multiplexes, understandably overshadowed the actual movie. It’s also held up incredibly well, mostly because Carrey and co-star Jeff Daniels are willing to do absolutely anything to make you laugh. Christopher Guest, Michael McKean, and Harry Shearer made musical and comedy history when they stepped into the leather boots of Spinal Tap, “one of England’s loudest bands.” While a lot of comedies from the ’80s are dated, this one still lands every single joke. The Interview

Remember the movie that almost started a war? Go ahead and watch it. OK, a lot of danger. Satirizing the Cold War this aggressively way back in 1964, Kubrick rewrote the textbook for political comedy and presented viewers with an instant classic that was both hysterical and terrifying. Consider this an entry that recommends watching all of them. Chasing Amy

Kevin Smith’s best film is also one of his most personal, the story of a man who falls in love with a lesbian and destroys his friendship in the process. When the President has a stroke, his double has to step in and take his place, but the new guy doesn’t exactly want to follow orders. Hepburn plays a divorced woman who is about to marry again when her ex-husband (Grant) and a reporter (Stewart) complicate things. When you think of Clouseau’s bumbling crime-solving, this is really where that began as Sellers’ work in the first film made the producers shift focus from David Niven’s charismatic criminal. It was actually pretty funny. It’s a smart, funny movie with a fan base that has only grown in the two decades since its release. Steve Martin stars as a filmmaker who is trying to make a film so low-budget that his star doesn’t even know he’s in the movie. Some of it is a bit dated now when it comes to social and class issues, but the cast and sharp writing for its era make it work. Strangelove or: How I Learned to Stop Worrying and Love the Bomb

The large fan base of Stanley Kubrick often mentions dark pieces of work like 2001, A Clockwork Orange, and The Shining, but one of his best and most influential films is a comedy about the end of the world. It’s sweet, smart, and funny. They drink a lot and generally hate the world. No one knew who Jon Favreau and Vince Vaughn were the day before Swingers came out, but it launched them into the celebrity sphere, where they still reside. Now that everyone feels ancient, take the nostalgic pick-me-up and watch this goofy comedy that announced the SNL star as a major movie talent. Smith has never been better than he is here at capturing believable, funny human relationships, and he gets his best acting work of his career as well from Ben Affleck, Joey Lauren Adams, and Jason Lee. Tom Cruise plays the title character, a sports agent who is pushed into starting his own agency while he falls in love with a single mother, played by Renee Zellweger. Austin Powers: International Man of Mystery

Mike Myers never could have imagined that his goofy superspy parody would launch a franchise, but all three films about Austin Powers are on HBO Max, just waiting for a rainy-day marathon. It’s really just a film about a believable woman and her daughters, but Holofcener and her cast find so much truth in the comedy to make these people feel real. 13 Going on 30

In the subgenre of body-swap comedies, this is one of the sweeter entries, a nice showcase for Jennifer Garner and one of the lighter pieces of escapism you can find on HBO Max. Garner plays a 13-year-old girl who wishes she could be popular and wakes up to find out that she’s now 30. It’s a simple movie that’s more reliant on witty dialogue and the texture of its setting than narrative, but it’s an incredibly smart, too, and earned Stillman an Oscar nomination for Best Original Screenplay. Waiting for Guffman

Arguably the best of the Christopher Guest ensemble improvised comedies. There are several Chaplin classics on HBO Max. North Korea will never know. High Fidelity

Stephen Frears directed an adaptation of the beloved 1995 Nick Hornby novel, and the result is one of the best films of John Cusack’s career. Just enough nostalgia and self-empowerment mix in this sweet fable that co-stars Mark Ruffalo, Judy Greer, and Andy Serkis. Bill & Ted’s Excellent Adventure

The 1989 flick stars Alex Winter and Keanu Reeves as the title characters, a pair of average California teens who go back in time to complete their high school history class presentation. *New additions are indicated with an asterisk. Billy Madison

Adam Sandler’s feature comedy debut is over a quarter-century old. This movie is still money, baby, as it captures the posturing of young men trying to get work and get laid in Hollywood in the mid-’90s. Muriel’s Wedding

This 1994 breakthrough for Toni Collette has maintained a loyal following for over a quarter-century for a reason, and it’s not just the great songs by ABBA. The Cable Guy

Coming off a wave of friendly blockbusters, Jim Carrey’s 1996 black comedy rubbed some people the wrong way. Clair (Guest himself) allows so many brilliant comedic talents a chance to shine, including Eugene Levy, Catherine O’Hara, Fred Willard, and Parker Posey. Singin’ in the Rain

Movies don’t get more delightful than this beloved classic about backstage drama on the advent of the talkie. Lovely and Amazing

Nicole Holofcener wrote and directed a great character study starring Catherine Keener, Brenda Blethyn, Emily Mortimer, and a young Jake Gyllenhaal. Services you subscribe to through our links may earn us a commission. Kline is joined by Sigourney Weaver, Frank Langella, Ving Rhames, Sir Ben Kingsley, and the late Charles Grodin in a comedy that’s really held up. Ryan and Crystal have arguably never been as charming as they are here, but it’s really Nora Ephron’s razor-sharp script that made this an instant classic. Rush Hour trilogy

Jackie Chan and Chris Tucker found a perfect comedy/action chemistry in three Rush Hour movies that played off their very different styles. The brilliant 1996 mockumentary about a community theater group led by the unforgettable Corky St. Hysterical and influential, Excellent Adventure has held up beautifully, and so has its sequel, Bill & Ted’s Bogus Journey, also on HBO Max. Get Shorty

Barry Sonnenfeld directed one of the better adaptations of an Elmore Leonard novel and anchored it with one of John Travolta’s most memorable performances. The truth is that while it’s not perfect, The Interview contains some inspired work from James Franco, and a great supporting turn from Randall Park as Kim. You can sign up here. Martin also wrote the script, which is razor sharp and consistently hysterical. The Oscar winner plays both the President of the United States and an ordinary guy who looks exactly like the leader of the free world. *Dr. Collette is delightful as a socially awkward young woman who moves to Sydney to start life anew away from her small Australian town. Just ignore (most of) the recent stuff and go back to the beginning with Happy Gilmore, which for my money is still Sandler’s funniest movie overall. Swingers

Every few years, a comedy comes completely out of nowhere and taps something in the zeitgeist that makes everyone involved a star. *A Shot in the Dark

The best movie in the Pink Panther franchise is actually the second one, this 1964 comedy classic, the movie that really defined the role of Inspector Clouseau as played by the amazing Peter Sellers. The story of a normal guy played by Ben Stiller (who also directed) who befriends a very abnormal guy is a classic for those who like their humor with a little bit of danger. The 1991 blockbuster comedy that was so popular that it won co-star Jack Palance an Oscar. HBO Max has one of the deepest and most impressive catalogs of any streaming service in the world, and their selection of comedies reflects the dense quality of their catalog overall. Grant plays one of two unemployed actors who share a flat in Camden in 1969 and head off on a weekend holiday. It’s a reminder of how great Costner could be in the right material. *The Wedding Singer

Billy Madison and Happy Gilmore had their fans, but it was 1998’s The Wedding Singer that really made Adam Sandler into a massive comedy star. Withnail and I

Bruce Robinson wrote and directed this 1987 black comedy, which became a massive cult hit in the era of VHS. When Harry Met Sally

Meg Ryan and Billy Crystal star in this 1989 rom-com that became an essential movie about whether or not men and women can truly be friends without romance entering into the picture. The Philadelphia Story

The 1940 George Cukor classic revitalized Katharine Hepburn’s career, but it also features incredibly charismatic performances from Cary Grant and Jimmy Stewart opposite her. Related

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Tags: The Producers

Shockingly, Mel Brooks’s directorial debut wasn’t that well received when it was released, but the film went on to develop a very loyal following over the years, leading to a Broadway musical version and even a remake.