Films: Sam Raimi’s Spider-Man trilogy (2002, 2004, 2007); various Spider-Man sequels, animated series, and video games
Role: J. Jonah Jameson, editor-in-chief at the Daily Bugle
Memorable line: Peter Parker: “You don’t trust anyone. That’s your problem.” J. Jonah Jameson: “I trust my barber.”
Toupee debate: In the Spider-Man: Far from Home (2019) and No Way Home (2021) films, J. Jonah Jameson is noticeably balding. When he was tapped to reprise the role, Simmons tried to negotiate to be able to wear a hairpiece, as he had for the Raimi films, but was vetoed.
Film: Whiplash (2014)
Role: Terence Fletcher, jazz conductor/teacher at Shaffer Conservatory
Memorable line: “Not quite my tempo.”
Notable injury: In the infamous “rushing or dragging” scene, the slaps Simmons gave to his co-star Miles Teller’s face were real. Teller also really tackled Simmons for the “Neiman, you’re done” scene — which caused Simmons to crack two ribs. Afterward, he still had to finish out the final two days of shooting.
Films: The Accountant (2016); The Accountant 2 (2025)
Role: Ray King, the U.S. Treasury guy who hunts down Ben Affleck’s character
Memorable line: “I spent my whole life only recognizing my lucky breaks after they were gone.”
Pep talk: During production for The Accountant, Simmons was asked to host Saturday Night Live for the first time, and he was nervous. His co-star Ben Affleck, who had hosted multiple times, helped coach him through what to expect.
Film: Juno (2007)
Role: Mac MacGuff, father of Juno
Memorable line: “Are you having boy troubles? Because I gotta be honest with you; I don’t much approve of dating in your condition, ’cause, well, that’s kind of messed up.”
Michigan connection: Kimya Dawson’s “Tire Swing,” which plays during the opening scene when Juno walks home after taking a pregnancy test, features keyboards from Michigan native folk punk singer-songwriter Paul Baribeau.
Series: Oz (1997-2003)
Role: Vernon Schillinger, head of the Aryan Brotherhood at the Oswald State Correctional Facility
Memorable line: “Shilling-er!” (correcting people who pronounce his name “Shillin-jer”)
20/20 hindsight: Simmons nearly turned down the role because he was worried it would result in his being typecast for the rest of his career.
Film: For Love of the Game (1999)
Role: Frank Perry, Detroit Tigers manager
Memorable line: “Let’s get outta here before we get our asses kicked twice in one night.”
Special delivery: Simmons had to leave the set temporarily during production because his son was born.
Film: Burn After Reading (2008)
Character: CIA superior; film critic Roger Ebert wrote of the nameless character: “The boss doesn’t have much dialogue, but every line is a punch line.”
Memorable line: “Report back to me when … uh, I don’t know. When it makes sense.”
Notable injury: During production for this Coen brothers release — starring Brad Pitt, George Clooney, and Frances McDormand — Simmons tore a few tendons while playing basketball with his son. As a result, he had to shoot some scenes with his hands folded in his lap in order to hide the cast on his thumb.
Film: Up in the Air (2009)
Role: Bob, an employee getting laid off by Ryan Bingham (George Clooney) and Natalie Keener (Anna Kendrick)
Memorable line: “Unemployment is what, 250 bucks a week? Is that one of your positive effects?”
Michigan connection: Part of the film takes place in Detroit, and some scenes were shot at the Detroit Metropolitan Airport.
Film: Red One (2024)
Role: Santa Claus
Memorable line: “Kavalame!” (the word he uses to command his reindeer)
A well-seasoned Santa: Simmons was no stranger to playing Old St. Nick when he signed on to this role — he previously voiced Santa in the Netflix animated film Klaus (2019), and one of his first gigs out of college was working as a mall Santa.
Film: Thank You for Smoking (2005)
Role: Budd “BR” Rohrabacher, Nick Naylor’s boss at the Academy of Tobacco Studies
Memorable line: “We don’t sell Tic Tacs, for Christ’s sake. We sell cigarettes. And they’re cool and available and addictive. The job is almost done for us!”
Big Tobacco meets Big Tech: Elon Musk and Peter Thiel — now known as top funders of conservative candidates and causes — along with fellow billionaire and “PayPal Mafia” member Max Levchin, are listed as executive producers on the film.
This story originally appeared in the September 2025 issue of Hour Detroit magazine. To read more, pick up a copy of Hour Detroit at a local retail outlet. Click here to get our digital edition.
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