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3 comedies on Amazon Prime Video you need to watch in May

Three men dressed casually with '80s haircuts walking down the street in a scene from Everybody Wants Some!!
Paramount Pictures

It’s never a bad time to watch a comedy. If you’re in a bad mood, a good comedy can lift your spirits. If you’re in a good mood, you’ll truly enjoy every laugh to the fullest. Maybe you want to watch from the hotel room while you relax after a long day at the beach on vacation, or you’re curling up with the family or on your own at home on a rainy Sunday. Whatever the reason or situation, we have you covered when it comes to some great comedies to check out this month.

There are three comedies on Amazon Prime Video you need to watch in May. One of them is a recent film that earned multiple Academy Award nominations, and toes the line between drama and comedy. Another is a hilarious ’80s-set movies about a bunch of college-aged baseball players getting up to trouble. The third is a stand-up special you can actually watch with the whole family. Read on to see if one or more of these are worth adding to your watch queue this month.

The Holdovers (2023)

THE HOLDOVERS - Official Trailer [HD] - In Select Theaters October 27, Everywhere November 10

Nominated for five Academy Awards including Best Picture, with Da’Vine Joy Randolph winning for Best Supporting Actress, The Holdovers was one of last year’s most critically acclaimed films. While it’s dubbed a Christmas comedy-drama, there’s no reason you can’t watch this movie any time of year.

Paul Giamatti stars as a classics teacher Paul Hunham in a boarding school in the ’70s who, after costing the academy money, is punished by having to chaperone a group of students over the Christmas break. Paul’s (Giamatti) strict teaching style doesn’t sit well with students and even fellow teachers, so it’s no surprise the kids are none too thrilled about the experience. Thankfully, a wealthy father of one of the kids eventually swoops in and takes the group on his family ski trip to get them out of the situation. All except, one, that is. Angus (Dominic Sessa) isn’t able to reach his parents to get permission and thus has to stay back. Together Paul, Angus, and the school’s cafeteria manager, Mary (Randolph), get up to various antics as they try to make it through the rest of the break.

Digital Trends’ Jason Struss says The Holdovers is the “next great Christmas movie classic,” calling Giamatti’s performance his best in years. Despite also being a drama, Struss says the movie is “incredibly funny” thanks to the profane banter among students and moments like the memorable road trip scene. Add The Holdovers to your holiday movie playlist, but don’t deny yourself the pleasure of watching it this month, too.

Stream The Holdovers on Amazon Prime Video.

Everybody Wants Some!! (2016)

EVERYBODY WANTS SOME Trailer (2016)

Set in 1980s Texas, Everybody Wants Some!! is about a group of college baseball players who get up to male jock debauchery when living together in an off-campus house. Rules are for other people, they believe, which means the strict no alcohol and no women upstairs policies are quickly thrown out the window, along with all the other no-nos that would otherwise prevent the boys from truly enjoying college life and all its spoils.

Everybody Wants Some!! has all the elements of a great teen comedy, from hook-ups to bar fights, rule-breaking to drunken parties, and an eclectic mix of characters, each with their own unique personalities and traits. The movie has a fabulous soundtrack from that era as well (think everything from The Knack’s My Sharona to Blondie’s Heart of Glass and Cheap Trick’s I Want You to Want Me). It’s just downright fun to watch.

Stream Everybody Wants Some!! on Amazon Prime Video.

Nate Bargatze: Hello World (2023)

Nate Bargatze: Hello World - Official Trailer | Prime Video

In the mood for stand-up comedy? Nate Bargatze: Hello World was Amazon Prime Video’s biggest original comedy special debut, according to Deadline, breaking records for the streamer. If you haven’t watched it yet, you’ll find Nate Bargatze: Hello World both highly entertaining and relatable, especially if you grew up in the ’80s and ’90s. Bargatze waxes poetic about growing up in a pre-tech generation and tackles topics like the challenges of marriage and being the first-born child in his family, recalling ridiculous things that have happened in his life.

For those who have kids, this special isn’t no-kids-allowed raunchy comedy. It’s actually rated 13+, so it’s family-friendly and appropriate to watch with older kids. A rarity nowadays, no controversy stemmed from this stand-up routine, either. It’s just good, old-fashioned jokes told in an engaging way that will entertain you during a night in with friends or loved ones.

Stream Nate Bargatze: Hello World on Amazon Prime Video.

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Christine Persaud
Christine has decades of experience in trade and consumer journalism. While she started her career writing exclusively about…
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