The actor revisits his chaotic MTV VJ era, his unexpected rise to fame, and the now‑iconic moment he and Tupac accidentally got high together on live TV.
Simon Rex may be busy collecting praise and accolades for his turn in Sean Baker’s Red Rocket, about a washed‑up porn actor returning to his Texas roots, but he’s still got time to go down Memory Lane and recall his own, more humble beginnings. In the mini‑doc Thru the Eras, Rex and friends like Regina Hall, Mark Ronson, and fellow former VJ Pauly Shore look back on how he wandered into a multi‑hyphenate career, one chance encounter after the next.
Before MTV came calling, Rex had a brief stint in the adult industry — something he has openly acknowledged over the years. Those early videos became unexpectedly popular thanks to his boyish, skater‑next‑door charm, a quality that would later help him stand out on MTV and in Hollywood. Rather than derail him, the experience became part of his unconventional, zig‑zagging path toward mainstream success.
First, fresh out of high school, he was dating a model when a casting agent noticed him — and he landed the job instead. That led to every young knockabout’s dream in the ’90s: joining MTV as a VJ. “He was like the cute, white boy with all the flavor on MTV,” says Hall.
Simon Rex’s 2000s Era Style — A Quick Breakdown
Before the viral moments and talk show stories, Simon Rex was very much a product of early-2000s MTV energy — relaxed, slightly chaotic, and effortlessly cool without trying too hard.
The vibe? Effortless, a little reckless, and very early-2000s MTV.
- Graphic tees and layered tanks
- Loose or straight-leg denim
- Track jackets or zip hoodies
- Skate-inspired sneakers
- Messy, undone styling that never felt overthought
It wasn’t polished — and that’s exactly why it worked. The look sits somewhere between skater, club kid, and off-duty MTV host. Today, you can still find modern versions of this style across streetwear and everyday essentials — especially in graphic tees, relaxed denim, and casual sneakers that carry that same early-2000s energy.
And then came the story that still feels too wild to be real.
As a VJ, Rex was at an event and, having clocked out of work, he and his producer were getting stoned when Tupac Shakur suddenly showed up — as iconic rappers tend to do. “And they’re like, ‘You have to interview Tupac now, live, on TV,’” Rex says. “And I said to my producer, ‘I’m too stoned.’ They go, ‘Don’t worry, so is he.’” In the MTV clip that follows Rex’s admission, it’s clear they’re both high as a kite and genuinely enjoying each other’s company.
From there, Rex went on to try his hand at acting, even reading for a role in Good Will Hunting. While it took him a while to be taken seriously as an actor, he also dabbled in music, rapping under the name Dirt Nasty. Among his fans, according to Mark Ronson, was the late Amy Winehouse.
The mini‑doc packs these stories — and plenty more bonkers detours — into five minutes of pure nostalgic chaos. It’s a reminder that Simon Rex’s career has never followed a straight line… and that’s exactly what makes him so endlessly watchable.
Watch the moments and relive the madness below.
See the original Entertainment Weekly interview over at: Red Rocket’s Simon Rex on his VJ career, interviewing Tupac
Join the conversation and tell us your favorite Simon Rex memory from the MTV era or those choice DVD’s.
