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The Best Comedies on HBO Max: Have You Watched 20th Century Terrific Comedy Yet?

The Best Comedies on HBO Max: Now that we all need HBO Max to watch the latest movies, it’s time to delve into the service’s vast catalog of titles to see what else it has to offer.

What could be more suitable than a terrific comedy after the last several years we’ve all had?

Fortunately, HBO has a plethora of options. Of course, there are new releases, but they also have a large selection of classic films, notably from the 1980s and 1990s.

Here are a few of your top options for a humorous night in. And this is only for the time being; new titles are being added all the time.

1. My Cousin Vinny (1992)

My Cousin Vinny is simply adorable, amusing, and incredibly intelligent. It masterfully blends two of my favorite genres — jargon-filled judicial procedurals and screwball fish-out-of-water comedies — to create a film that feels like it’s no longer made.

After two New Yorkers (Ralph Macchio and Mitchell Whitfield) are arrested for the murder of an Alabama convenience store clerk, they enlist the help of Macchio’s cousin Vinny, played by Joe Pesci, who is having the time of his life.

Vinny is a lawyer, but one who has only recently passed the bar and is used to low-stakes cases in Brooklyn rather than straight-up murder trials in a foreign state.

It’s pure fun to watch Pesci jump through all the legal hoops with his never-ending, mildly annoying brand of charisma.

Don’t even get me started on Marisa Tomei’s stunning performance. Her sparring/loving with Pesci is a two-hander for the ages, and she won an Oscar for it (sigh, remember when the Oscars cared about comedy?).

2. Best in Show (2000)

One of the best comedies ever filmed is Best in Show. The film, which was released in 2000, is portrayed as a fictional documentary of people preparing for and competing in the Mayflower Kennel Club Dog Show, and it follows filmmaker Christopher Guest’s “mockumentary” technique.

The ridiculousness of the situation, as well as dog grooming in general, serves as a backdrop for the film’s colorful characters, with this truly excellent cast delivering a slew of hilarious performances.

In any other film, each character would most certainly steal the comic scene, but in Best in Show, these MVPs are all joined together to form a humorous tour de force.

3. Coming To America (1988)

When Eddie Murphy starred in 48 Hours, Beverly Hills Cop, and Trading Places, he was on top of the world.

He had departed his acclaimed place on Saturday Night Live four years previously and had starred in a slew of smash comedies in the interim, including 48 Hours, Beverly Hills Cop, and Trading Places.

Despite the fact that Coming To America is undoubtedly his most well-known comedy (and even spawned a sequel in 2021, but the less said about that one the better).

Instead of being in a forced arranged marriage, Prince Akeem (Murphy) of Zamunda travels to America to find himself a woman who is clever, strong-willed, and will assist him to control his African country when he is proclaimed King.

Coming To America is also one of the best demonstrations of Murphy’s range as a comedy actor, as he not only plays Akeem, but also the lead singer of a soul band called Sexual Chocolate (really, that is the name), an elderly Jewish man, and an elderly barber shop owner.

4. Safety Last! (1923)

You’ve surely heard of Charlie Chaplin, and you’ve probably heard of Buster Keaton as well. Harold Lloyd, another great voice from the silent era, can also be discovered thanks to HBO Max.

Because of its memorable ending, in which Lloyd hangs from the minute hand of a ticking clock, Safety Last! is a great place to start.

If you haven’t seen it, you’ve undoubtedly seen it ripped off. Even though the film is nearly a century old, you’ll be amazed at how they achieved the impression. But the film isn’t only about the risky clock tower antics; the rest of it is fantastic as well.

The plot revolves around a man wanting to make enough money in the big city to eventually propose to his sweetheart, a goal that lands him in all kinds of difficulties for our entertainment. Lloyd possesses a certain everyman appeal that is difficult to dislike.

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5. A Hard Day’s Night (1964)

The Beatles are a band from the United Kingdom. What was it that they couldn’t do? It should be enough that they are the greatest rock band of all time. But, no, they turned out to be quite amusing as well.

A Hard Day’s Night, directed by Richard Lester, demonstrates this by giving each of the Beatles (particularly Ringo) his own showcases in which to flaunt their personalities, acting skills, and comedic chops.

Meanwhile, the picture features a plethora of terrific music to complement the still-effective comedic segments.

A year later, Lester and the band would reunite for the larger Help! But there’s a reason this is the gold standard of rock and roll movies.

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6. Tampopo (1985)

Anyone who appreciates eating (which is pretty much everyone) should see this 1985 Japanese film, which celebrates the act of eating in pretty much every way possible.

Tampopo is a film about a woman who is trying to improve her ramen recipe (with the help of a young, dashing Ken Watanabe) and is interspersed with short vignettes about beautiful, glorious food.

It’s almost as if the movie Kentucky Fried Movie was actually about Kentucky Fried Chicken. There’s a little bit of everything in this film: thrills, cute kids, sex, gangsters… But, most importantly, it’s hilarious. Just don’t try to watch it if you’re hungry.

7. Tootsie (1982)

Tootsie is unafraid to be charming as hell, honest as hell, and unsparingly spiky as hell, which I believe is the secret to her success. Let’s be honest:

A 1982 comedy directed by a straight white male (Sydney Pollack) about a straight white actor (Dustin Hoffman) who turns to drag to gain work should have been a cringe-worthy disaster riddled with casual homophobia, misogyny, and short-sighted shenanigans.

Instead, Pollack lets us see how much of a pretentious jerk Hoffman’s character is before the disguise, how lovely but complicated Jessica Lange is throughout, and how systemic misogyny is present in every aspect of American culture, including the entertainment industry.

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