In 2021 alone, the respected 66-year-old actor appeared in Zack Snyder’s Justice League, voiced characters in animated fare such as Invincible, Infinity Train, and The Great North, and still has blockbusters The Tomorrow War and Spider-Man: No Way Home on tap. And while it’s easy to single out his Oscar-winning performance in 2014’s Whiplash as a crowning achievement, Simmons still maintains a certain fondness for his portrayal of J. Jonah Jameson in Sam Raimi’s previous Spider-Man trilogy. “Those movies with Sam will always be big highlights of my career and my life,” Simmons tells Den of Geek during a recent Zoom call. “Sam is one of my favorite directors and human beings.” Simmons, whose career took off after playing the abrasive Daily Bugle editor in Raimi’s three Spider-Man movies—if you squint you can even see some parallels between JJJ and Whiplash’s Fletcher—was notably absent from Marc Webb’s webslinger 2012 reboot starring Andrew Garfield. In fact, Jameson was never even part of the storyline of those movies beyond one shoehorned email exchange in The Amazing Spider-Man 2. Audiences were simply left to assume the Daily Bugle’s grouchy editor-in-chief became the victim of a narrative shake-up, and wonder just who could ever fill Simmons’ shoes in that iconic role. “To have the opportunity to kind of do a reboot of the character, I was eager to hang on to the things I really loved about it and totally open to letting go of some of that, and realizing we are in a more updated version of that universe,” Simmons tells us now. “Hopefully, we found the sweet spot there.” Indeed, moviegoers were thrilled to see Jameson once more on the big screen and, as ever, fixated on Spider-Man. And they will get to see even more of him in December’s Spider-Man: No Way Home. Simmons compared his first iteration of Jameson to the newer interpretation and found there wasn’t much difference. Well, except for the recognizable flattop haircut that has been replaced. “Mostly just the hair, or the lack thereof,” says Simmons about the differences in his interpretations. Over the five movies, Jameson has remained a cigar-chomping hothead, quick to label Spider-Man as a menace. And while that brashness serves as part of the character’s charm and DNA, Simmons doesn’t need the writers to flesh Jameson out or give him more layers. “For a lot of characters, that evolution is a really important aspect,” Simmons concludes. “I like the lack of evolution of that character. There are ways that he’s evolved, but he’s the same blowhard… and that’s what I enjoy doing.”