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Leaves of Grass (2009) As an actor, Tim Blake Nelson has worked closely with the Coen brothers, and he brings a Coen-esque quality to his fourth film as a writer-director, starring Edward Norton in dual roles as a renowned Ivy League philosophy professor and his ne’er-do-well pot-dealing twin brother. Deceptively devious Brady lures the uptight Bill back to their Oklahoma hometown and ropes Bill into participating in a scheme to get some nasty characters off Brady’s back. The initially antagonistic brothers reconnect over some high-quality bud, while Bill reluctantly learns to appreciate the Southern life he left behind. Nelson (who also plays a supporting role) makes some broad thriller-style swings in the movie’s second half that don’t quite pay off, but the laidback scenes of family togetherness (featuring Susan Sarandon, Keri Russell and Melanie Lynskey as the women in the brothers’ lives) have just the right amount of warmth and wit.

A Very Harold & Kumar Christmas (2011) The first Harold and Kumar adventure, 2004’s Harold & Kumar Go to White Castle, is justifiably beloved, and the second, 2008’s Harold & Kumar Escape From Guantanamo Bay, is justifiably scorned. But the third movie rarely gets its due as both a new holiday classic and a surprisingly poignant conclusion to the story of pot-smoking best friends Harold (John Cho) and Kumar (Kal Penn). With a madcap quest storyline (to replace a destroyed Christmas tree) similar to the first movie’s journey to White Castle, plus an examination of how friends can grow apart as they grow older (and one retains a certain recreational habit while the other doesn’t), Christmas brings the laughs and the pathos, anchored by the enduring, appealing chemistry between the two leads.

The Wackness (2008) Teenager Luke Shapiro (Josh Peck) spends the summer of 1994, after his senior year of high school, dealing weed out of a portable ice cream cart, falling in love with his classmate Stephanie (Olivia Thirlby) and bonding with his psychiatrist and top client Dr. Squires (Ben Kingsley) in this wistful coming-of-age dramedy. Peck and Thirlby make for a winning teenage couple, and Kingsley has a lot of fun as the dissolute, melancholy adult whose only friend is his teenage drug dealer. Writer-director Jonathan Levine infuses the movie with nostalgia for the New York City of the ’90s, with all its flaws and opportunities, but more than that he captures that liminal time between the end of adolescence and the beginning of adulthood, when life is full of possibilities but also full of potential disappointment.

Richard Linklater’s 1993 high school ensemble comedy Dazed and Confused is justifiably considered a classic, but this “spiritual sequel” set in 1980 (just a few years after Dazed’s late-’70s time period) has many of the same charms, with its authentic portrait of college baseball players hanging out and goofing off in the few days before the start of their freshman year. Of course, that involves smoking plenty of pot, and Wyatt Russell steals every scene he’s in as the main characters’ marijuana guru, who introduces them to new ways of smoking and new philosophical ideas about the universe. As he does in Dazed, Linklater captures the everyday feel of the time period, not just the fashion and the music, with grounded characters you’d want to spend time with, and a warm, casual vibe.

Dude (2018) The stars of comedies about young people hanging out and smoking pot are almost always dudes, but Olivia Milch’s directorial debut Dude flips the formula by starring a quartet of young ladies. Lucy Hale, Kathryn Prescott, Awkwafina and Alexandra Shipp play four high school seniors who are all facing uncertainties as they move on to a new phase of their lives—but one thing they’re never uncertain about is their love for smoking together. The mix of exuberant comedy and stark drama is sometimes uneven, but the four leads are all immensely appealing, and at its best Dude is an affecting teen hangout movie that takes teenage problems seriously, with room for both silly rap sing-alongs and heartfelt talks about grief, privilege and sexual exploration.

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Everybody Wants Some!! (2016)

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Inherent Vice (2014) Serious film auteur Paul Thomas Anderson adapting serious novelist Thomas Pynchon sounds like a recipe for a heavy, serious movie, but while Inherent Vice can be a bit narratively overwhelming as its plot twists pile up and its running time heads past two hours, it’s mostly a lighthearted lark. A sunny Southern California mystery in the vein of The Long Goodbye or The Big Lebowski, Vice stars Joaquin Phoenix as pot-smoking private investigator Doc Sportello, who gets in way over his head when he’s hired to look into the disappearance of a real estate mogul. As the story gets increasingly incomprehensible, Doc is as baffled as the audience, but his laid-back, chemically enhanced approach to life allows him to come out on top of the various nefarious characters he encounters, even if he doesn’t always understand how he does it.

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