Ultra Fun Movies from the 2000s on HBO Max
Undercover Brother (2002)
Undercover Brother takes the soul and style of traditional ’70s Blaxploitation and infuses it with modern comedic satire on cultural and racial perceptions and stereotypes. It doesn’t take itself too seriously, being self-aware in its absurdity. It’s an essential volume in the Black comedy collection, with plenty of iconic faces to boot: Eddie Griffin, Dave Chappelle, and Neil Patrick Harris, to name a few.
John Tucker Must Die (2006)
Archetypal cliquey tropes turn to a unified girl squad over the cocky, womanizing titular “hot guy” John Tucker. A vegan, a cheerleader, an overachiever, and the new girl in school: what could they possibly have in common except for a man?! As they soon find, it’s more than they think, and it includes righteous, riotous modes of revenge. It surely doesn’t pass the Bechdel test, but nonetheless, it’s a hilarious capsule in the teen movie catalog.
Malibu’s Most Wanted (2003)
Malibu’s Most Wanted is a comedic dive into the hapless insanity of cultural appropriation, especially in the context of wealthy white men positioning themselves as products of “the streets.” Jamie Kennedy’s Brad Gluckson is a spoiled governor’s son desperate to be the next hip hop star. “B-Rad G” is the Chet Hanks before Chet Hanks, if you will, but even more unhinged.
Final Destination (2000)
2000s horror doesn’t get enough credit, but the decade brought us one of the most iconic horror franchises to date. Rube-Goldberg-style death traps motivated by Death’s own decision keeps anxiety high without losing the fun factor. With Tony Todd, Devon Sawa, and Sean William Scott as just a few familiar faces, Final Destination maintains its integrity while also feeling as 2000s as a movie can get.
Eight Legged Freaks (2002)
This film blessed me with arachnophobia at the ripe age of five, but now it’s a film to watch for fun instead of for fear. Eight Legged Freaks is the type of B-horror campy comedy to alleviate a long day’s boredom or stress. David Arquette and co. (including a young Scarlett Johansson) versus truck-sized spiders…it pretty much sells itself.
— Peyton Robinson
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Deadwood (2004)
Has an appearance on a Star Wars show recently brought Timothy Olyphant back into your life? Does it have you considering a revisit of one or two of his great dramatic small-screen works? Try Deadwood. It also has Ian McShane. And a movie!
I May Destroy You (2020)
Michaela Coel’s breakout series is likely going to appear on many a critic’s best TV shows list for 2020. It’s a raw, unflinching comedy-drama that explores the story of a survivor of sexual assault. And it’s brilliant.
The Sopranos (1999)
Awaiting you elsewhere on HBO Max — over the river into New Jersey, at the very least — are eighty-six episodes of pure brilliance from creator David Chase and an amazing cast led by the late James Gandolfini. It’s a show that had the likes of Terence Winter (Boardwalk Empire) and Matthew Weiner (Mad Men) among its creative team. Plus, there’s a prequel movie coming in 2021 about Young Tony Soprano. Consider this homework.
The Wire (2002)
One of the greatest television shows of all-time. Ask anyone who’s seen it. Set in Baltimore, Maryland, each season of David Simon’s incredible show looks at the city from a different angle — from the drug trade to the workings of a seaport to the education system. It’s a dense, incredibly well-acted show that absolutely sticks the landing.
Watchmen (2019)
Damon Lindelof’s 2019 series was a hit with critics and a massive surprise for fans of Alan Moore’s classic book, and it ultimately took home the Emmy for Outstanding Limited Series. It also took home ten other Emmys, including an incredibly well-deserved Outstanding Leading Actress win for Regina King. With an eight-episode season that absolutely rips, now is a better time than ever to watch the Watchmen.
— Neil Miller
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