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VOICE OVER: Rebecca Brayton WRITTEN BY: Timothy MacAusland
This legendary comedian has gifted the world plenty of epic performances over his long career. For this list, we'll be looking at Jack Black's best movie characters. Our countdown includes “Nacho Libre”, “High Fidelity”, “Kung Fu Panda” franchise, and more!

#10: Ignacio [aka Nacho]

“Nacho Libre” (2006) “Nacho Libre” as a whole may not be the worthiest followup to “Napoleon Dynamite” for director Jared Hess, but it similarly has one uber-memorable title character. In this one, Black plays a Catholic friar named Ignacio who pursues his dream of being a luchador to support a struggling orphanage. Ignacio is naturally torn between his pacifistic upbringing and his secret double life as Nacho. But it’s Black’s endlessly quotable lines that keep this one at the forefront of our childhood memories. Seriously, we can’t put on stretchy pants without thinking of this one. And you’d be lying if you weren’t shouting this back in 2006: “Nachooooooooo!”

#9: Miles

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“The Holiday” (2006) While we typically associate Jack Black with outlandish comedic characters, he’s shown on more than one occasion that he’s able to play things more grounded, too. And for anyone who thought he couldn’t pull off a love interest in a romantic comedy, think again. Here, Black plays Miles opposite Kate Winslet’s Iris, who’s having trouble forgetting her cheating ex, Jasper. Eventually, Miles too uncovers his own partner’s infidelity, prompting him and Iris to bond over their shared woes. Kate Winslet would be a daunting scene partner for any actor, but Black oozes chemistry alongside her. He might not have done something like this since, but even this is evidence of his sheer versatility.

#8: R. L. Stine & Slappy

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“Goosebumps” franchise (2015-18) Jack Black didn’t star in many high-profile movies in the early 2010s, so imagine our glee when he showed up to play “Goosebumps” author R. L. Stine in this throwback adventure. Sure, Black doesn’t resemble Stine whatsoever, but credit him for being able to craft a character that seamlessly slides into the film’s kooky universe. As if that wasn’t good enough, he pulls double duty by voicing the book series’ most iconic villain, Slappy the Dummy. Seriously, we’re getting Black at 200% capacity here, as he’s clearly having a blast playing off himself. While he only appeared in a cameo in the 2018 sequel, “Haunted Halloween,” we did get a similar role that same year in “The House with a Clock in Its Walls.”

#7: Barry Judd

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“High Fidelity” (2000) While Jack Black was definitely around in the ‘90s, he didn’t officially “arrive” until 2000’s “High Fidelity,” a fact even he recognizes. And how could he not, seeing as how good he is in it. This time playing the wacky best friend in a subversive romantic comedy, Black repurposes and makes the archetype his own, transforming it into something wholly idiosyncratic. Indeed, Barry has all the untamped spirit of a ‘70s-era punk band, and he won’t hesitate for a second to let his music tastes be known. As solid as lead John Cusack is, too, Black simply puts forth a presence that demands to be seen and felt, continually giving the tempo of the film the shot of adrenaline it needs.

#6: Bowser

“The Super Mario Bros. Movie” (2023) Illumination’s “Super Mario Bros. Movie” received some casting flak right out the gate. But one choice that worked beautifully is Jack Black as Bowser. While the King of the Koopas isn’t quite as gruff-sounding here as he is in the games, Black’s able to imbue the right amount of energy to prop up the character’s presence whenever he’s onscreen. Nailing the villain’s classic intimidation, Black also helps craft Bowser’s more insecure and softer side. After all, at the end of the day, he’s just a big ol’ turtle pining after a pretty blonde. We don’t know whose idea it was to have Bowser sing a Jack Black-esque love ballad, but it is everything.

#5: Jeff Portnoy

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“Tropic Thunder” (2008) If there’s one thing Jack Black’s filmography was missing, it was an action comedy. A meta movie through and through, “Tropic Thunder” has Black playing an entitled moviestar who’s made a career out of wearing fat suits and playing numerous characters in gross-out comedies. But when production on his Vietnam War movie takes him into the actual jungle, he’ll have to become a real soldier. The film’s entire cast is solid, and Jeff’s manic energy as he goes through withdrawal is the powder keg every scene needs. Seriously, Jeff Portnoy may be Jack Black’s zaniest character, but that doesn’t make him any less hilarious.

#4: Professor Sheldon “Shelly” Oberon

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“Jumanji” franchise (1995-) Apparently, there’s something about putting Jack Black in the jungle that just works. Here, Black plays a video game avatar who’s subsequently embodied by characters from the real world. As such, he has to convincingly deliver multiple personalities, which is no easy feat. Seriously, we didn’t think Jack Black essentially playing a teenage girl would be as hysterical as it is, but here we are. In the sequel, Black’s Shelly is this time embodied by the hulking Fridge, and he doesn’t miss a beat. But at the end of the day, Bethany realizes she and Shelly were meant to be. We really hope they make another one of these just so we can see Black in that silly hat again.

#3: Bernie Tiede

“Bernie” (2011) “Bernie” is unlike any other Jack Black movie, and it has a performance that’s had many critics calling it his best. Like “Goosebumps,” this one has Black playing a real-life figure in Bernie Tiede. Unlike “Goosebumps,” though, the story is of a much darker variety, as it depicts Tiede’s murder of his elderly companion, Marjorie Nugent. What makes the movie and the true story so fascinating is Tiede’s stellar reputation in the community as one of the nicest people you’ll ever meet. Black is so good at conveying this to the point that you almost empathize with Bernie relative to the exceedingly unpleasant Marjorie. This is where fact and fiction wonderfully coalesce, and at the center is one incredible performance.

#2: Po

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“Kung Fu Panda” franchise (2008-) As good as he is in all his animated roles, we refuse to believe Po could’ve been played by anyone but Jack Black. Put simply, “Kung Fu Panda” wouldn’t be what it is without the titular character. He’s goofy, passionate, and a little bit insecure, but Black’s able to convey all of that through Po’s surprisingly profound arc in all the outings. It’s the ultimate zero-to-hero story, and it simply wouldn’t work without making the character instantly relatable. Black’s not only able to do that with his innate charm and charisma, but he also manages to imbue a healthy amount of humanity as well, despite Po being a panda. Before we unveil our top pick, here are a few honorable mentions. Lance Brumder, “Orange County” (2002) Black’s Slacker Older Brother Is the Perfect Comedic Foil Lenny, “Shark Tale” (2004) Black Goes All In With This Affectation Carl Denham, “King Kong” (2005) A Much-Needed Humorous Presence in the Film JB, “Tenacious D in The Pick of Destiny” (2006) How Could We Not Recognize His Tenacious D Roots? Jerry Gerber, “Be Kind Rewind” (2008) Black Helps Make This Cult-Classic Classic

#1: Dewey Finn

“School of Rock” (2003) Okay, forget Po - THIS is the role Jack Black was born to play. A wannabe rocker, Dewey Finn is by all means washed up when he starts impersonating his roommate as a prep school substitute teacher. However, what starts as a scheme to get a quick buck turns into something special as Dewey makes a connection with his students over their shared love of music. “School of Rock” is probably the edgiest kids movie we were ever allowed to watch, but it works both then and now thanks to Black’s immense personability and zeal. Not only that, but he has such an outstanding rapport with his young co-stars that we want Dewey as our teacher ASAP. Class dismissed.

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