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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. There’s a little bit of something for anyone looking for something to make them laugh, from silent classics to recent hits. Pick your favorites, and then come back here for more.
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. Just enough nostalgia and self-empowerment mix in this sweet fable that co-stars Mark Ruffalo, Judy Greer, and Andy Serkis.
Long before he tackled Harry Potter, Chris Columbus made his directorial debut with this 1987 comedy about a long night for a Chicago babysitter. Elisabeth Shue plays Chris Parker, a 17-year-old who gets stuck babysitting an eight-year-old girl and eventually her 15-year-old brother. She ends up taking them downtown to save a friend and, well, things don’t go well.
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. The film features fantastic work from Paul Giamatti, Hope Davis, Judah Friedlander, and James Urbaniak, who plays the inimitable Robert Crumb.
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. The reason these movies work is Myers’s complete fearlessness — he’ll do anything to make you laugh.
Movies don’t get funnier than Christopher Guest’s brilliant mockumentary about people obsessed with their canine counterparts. 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 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. Hysterical and influential, Excellent Adventure has held up beautifully, and so has its sequel, Bill & Ted’s Bogus Journey, also on HBO Max.
Adam Sandler’s feature comedy debut is over a quarter-century old. 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. It really defined his man-child persona, one that he’s still working to this day.
One of Eddie Murphy’s top performances is in this 1999 satire from the great Frank Oz. 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. Martin also wrote the script, which is razor sharp and consistently hysterical.
Coming off a wave of friendly blockbusters, Jim Carrey’s 1996 black comedy rubbed some people the wrong way. Those people were wrong. 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. OK, a lot of danger.
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. 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.
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. There are several Chaplin classics on HBO Max. Consider this an entry that recommends watching all of them.
Billy Crystal was at the peak of his fame here. The 1991 blockbuster comedy that was so popular that it won co-star Jack Palance an Oscar. 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.
Kevin Smith rocked the indie-filmmaking world with a comedy that was shot for almost nothing and became a worldwide hit. 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.
Robert Zemeckis (Back to the Future) directed this twisted horror comedy way back in 1992 and its themes of superficiality and wealth have kept it current, along with fearless performances from Meryl Streep, Goldie Hawn, and Bruce Willis. The two actresses play rivals who drink a potion that promises eternal youth, and things get zanier from there.
One of Albert Brooks’s best films, this 1991 comedy is about a man (played by the writer-director) who dies and discovers that the afterlife includes a trial where one must answer for their life decisions before moving on to the next plane of existence. Brooks is charming, as is the wonderful Meryl Streep.
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. 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.
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. 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.
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. It’s a perfectly calibrated comedy with phenomenal performances all around, including Rene Russo, Danny DeVito, Delroy Lindo, and Gene Hackman. (The sequel, Be Cool, is also on HBO Max.)
Netflix may have all those new Adam Sandler comedies, but HBO Max has the classics. 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.
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. The actor plays Rob Gordon, a Chicago music store owner who struggles with relationships and responsibility. It’s a smart, funny movie with a fan base that has only grown in the two decades since its release.
Only two-thirds of what is referred to as Edgar Wright’s Cornetto Trilogy is on HBO Max (The World’s End is missing), but Hot Fuzz is probably the best of the bunch anyway, so it’s okay. The movie is not just a parody of dumb action movies but a love letter to flicks like Point Break and Bad Boys too. The best parodies come from fandom, and this is definitely one of the best.
Remember the movie that almost started a war? It was actually pretty funny. 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. 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. Go ahead and watch it. North Korea will never know.
Lovely and Amazing
Nicole Holofcener wrote and directed a great character study starring Catherine Keener, Brenda Blethyn, Emily Mortimer, and a young Jake Gyllenhaal. 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.
Whit Stillman made his directorial and screenwriting debut with this clever 1990 film about a group of rich kids in Manhattan. 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.
Martin Brest directed one of the best ’80s buddy comedies in a charming gem that paired Robert De Niro and Charles Grodin. The Oscar winner plays a bounty hunter assigned to bring back Grodin’s embezzling accountant, who stole money from the Chicago mob. Grodin and De Niro have perfect comic chemistry.
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. Collette is delightful as a socially awkward young woman who moves to Sydney to start life anew away from her small Australian town. It’s a delightful comedy about a memorable oddball.
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. Hepburn plays a divorced woman who is about to marry again when her ex-husband (Grant) and a reporter (Stewart) complicate things. It’s clever in ways that would redefine comedy, and it’s still influencing the genre.
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. 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.
*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. Chan’s incredible action skills are balanced perfectly by Tucker’s rapid-fire comedy delivery. The first movie is still the best, but HBO Max has all three if you’re in the mood for a marathon.
The true genius of Edgar Wright’s 2004 horror-comedy is that it takes both sides of its clever genre coin completely seriously. Yes, the story of a zombie attack on a small British town is laugh-out-loud hysterical, but this is also a legitimately great horror movie at the same time. It kicked off Wright’s Cornetto Trilogy, followed by the also-fantastic Hot Fuzz (also on HBO Max) and The World’s End.
Movies don’t get more delightful than this beloved classic about backstage drama on the advent of the talkie. 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. It’s joyous from front to back.
Every few years, a comedy comes completely out of nowhere and taps something in the zeitgeist that makes everyone involved a star. 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. 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.
All mockumentaries owe a massive debt to Rob Reiner’s 1984 directorial debut. 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.
Arguably the best of the Christopher Guest ensemble improvised comedies. The brilliant 1996 mockumentary about a community theater group led by the unforgettable Corky St. Clair (Guest himself) allows so many brilliant comedic talents a chance to shine, including Eugene Levy, Catherine O’Hara, Fred Willard, and Parker Posey.
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. 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.
Bruce Robinson wrote and directed this 1987 black comedy, which became a massive cult hit in the era of VHS. The wonderful Richard E. Grant plays one of two unemployed actors who share a flat in Camden in 1969 and head off on a weekend holiday. They drink a lot and generally hate the world. Everyone could see a little of these two nihilists in themselves.
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