The actor shares the hilarious backstory during a lively “Simon Says” segment on Drew’s daytime show, blending Hollywood charm with reality‑TV chaos.
The forevermore perpetual hottie Simon Rex stopped by The Drew Barrymore Show for a spirited round of “Simon Says,” Drew’s playful true‑or‑false game where the stakes are high and the audience is rooting for a prize. Before the questions even began, Drew teased him about his name — “How many times did you get Simon Says on the schoolyard?” — to which Simon laughed, “All the time. I still do.”
But the real magic hit when the wall revealed the first prompt: “I introduced Leonardo DiCaprio to the Jersey Shore cast at a club.” Drew guessed true — and Simon confirmed it with a grin.
Related Story: Simon Rex Looks Back on His Wild MTV Days and Tupac Moment
He dove into the story: he was out in L.A., bouncing between tables, when Leo spotted the Jersey Shore crew across the room. “Is that the Jersey Shore guys over there?” Leo asked — and then admitted he watched the show. “I want to meet them.” So Simon escorted him over, and the cast was blown away that DiCaprio not only recognized them but wanted to hang out. Simon joked that once the introductions were made, he “just sat back like, I did my work. I’m done here.”
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.
The game rolled on with more unexpected truths — including Simon revealing he once worked at a potato sack factory, clocking in like a Depression‑era laborer and cleaning machines filled with perforated potato‑bag dust. Drew was stunned, the audience screamed, and Simon laughed through the memory.
The final question? Whether he lost all the toenails on his right foot at Burning Man. Drew guessed false — and she was right, sending the entire audience home with gift cards. The relief on her face was priceless.
Before wrapping, Simon shared what’s next for him: stepping into producing. His first film, Operation Taco Garry’s, a conspiracy‑theory comedy, is hitting Amazon on March 24 and select theaters now. Drew cheered him on, celebrating his new creative chapter.
See how the moment played out below — the outcome is worth the watch.
Join the conversation and tell us your favorite part of Simon’s wild Drew Barrymore moment.
