Before he was the cigarette-smoking, whiskey-swilling king of Madison Avenue, Jon Hamm was just a guy with a really bad haircut. He was 25. He was a waiter. Honestly, he looked like he was trying out for a role in a middle-school production of Grease but accidentally walked into a hair salon and asked for the "floppy mushroom."
In 1996, the world was introduced to Hamm on a short-lived USA Network program called The Big Date. It wasn't exactly The Bachelor. It was more of a low-budget, neon-lit, mid-90s fever dream hosted by Mark L. Walberg. No, not the Funky Bunch guy—the Antiques Roadshow guy.
Why the Jon Hamm Dating Show Clip Went Viral
You’ve probably seen the grainy footage. It resurfaced in 2014, right as Mad Men was winding down, and the internet basically imploded. It’s hard to reconcile the debonair Don Draper with the guy in the periwinkle shirt who used the word "fabulosity." Seriously. He actually said it.
The premise of the show was simple. One woman gets to grill three guys to see which one earns a date. In this specific episode, the woman was Mary Lou Carter (now Mary Lou Sandler). She was a 25-year-old student and actress with a self-proclaimed foot fetish.
When Walberg asked Hamm how he would impress Mary, his answer was legendary for all the wrong reasons:
📖 Related: Benjamin Kearse Jr Birthday: What Most People Get Wrong
"Well, you start off with some fabulous food, then some fabulous conversation, with a fabulous foot massage for an evening of total fabulosity."
He said it with a straight face. It was earnest. It was cringe-inducing. It was 1996.
The Rejection Heard 'Round the World
Most people assume Jon Hamm won. He's Jon Hamm! He’s got that jawline that could cut glass. But in 1996, Mary Lou wasn't feeling the "fabulosity." She passed him over. Twice.
Actually, she chose a guy named Marc, a stuntman who promised to show her his "flexibility." Hamm didn't just lose once; he was rejected by a second contestant named Shonia later in the same episode.
👉 See also: Are Sugar Bear and Jennifer Still Married: What Really Happened
What happened to the woman who rejected him?
Mary Lou Sandler eventually did an interview with Salon after the clip went viral. She admitted she didn't even remember him. She was busy. She didn't have a TV. She told the press she was happily married to a "rock star" and wouldn't trade her husband for "a thousand Jon Hamms."
It’s a healthy perspective. At the time, Hamm was just another struggling actor in Los Angeles. He had moved from St. Louis with $150 and a 1986 Toyota Corolla. Success wasn't a guarantee. In fact, his agency, William Morris, actually dropped him in 1998 because he couldn't land a job for three years.
The "Butt Cut" and the Struggle for Work
Hamm’s appearance on The Big Date highlights a weird era in Hollywood casting. During the late 90s, the "Dawson’s Creek" look was king. Casting directors wanted boys. They wanted tiny guys with soft features.
Hamm didn't look like a boy. He looked like a 40-year-old man by the time he was 20. He has often joked that he spent his 20s auditioning to play the dads of people his own age. The "butt cut"—that middle-parted, floppy hairstyle—was his attempt to fit in. It didn't work.
✨ Don't miss: Amy Slaton Now and Then: Why the TLC Star is Finally "Growing Up"
The clip eventually found its way into pop culture history in a brilliant way. Tina Fey and the writers of Unbreakable Kimmy Schmidt used the actual footage in Season 4. They edited Hamm’s name tag to read "Richard" and used it as a "backstory" for his character, the Reverend Richard Wayne Gary Wayne. It turns out Hamm is remarkably good at making fun of his younger self.
Lessons from the "Fabulosity" Era
Looking back at the Jon Hamm dating show appearance isn't just about the cringe. It’s actually a pretty decent reminder of how much "the look" of the moment dictates success in entertainment.
- Persistence pays off: Hamm didn't get his big break in Mad Men until he was 36.
- Trends are temporary: The hair that was "cool" in 1996 looked ridiculous by 2007.
- Rejection isn't final: Getting dumped on a cable dating show didn't stop him from winning two Emmys.
If you’re feeling stuck or embarrassed by something you did a few years ago, just remember that somewhere on a server in a basement, there is footage of one of the world's most famous leading men offering a "fabulous foot massage" to a stranger for a chance to win a trip to Universal Studios.
If you want to track down the full episode, search for The Big Date Episode 50. It’s a time capsule of bad fashion, weird pickup lines, and the humble beginnings of a TV icon. For those looking to improve their own "fabulosity," maybe stick to the food and conversation and leave the foot massages for the second date.
If you’re curious about other stars who started on game shows, you might want to look into the early appearances of Paul Rudd or Aaron Paul. They all had to start somewhere, usually under some very bright, very unflattering studio lights.