Jay Leno reunites with former Tonight Show intern Ross Mathews 20 years later on The Drew Barrymore Show

More than 20 years after getting his start as an intern on The Tonight Show, Ross Mathews had a surprise reunion with his former boss Jay Leno. 

As part of a field assignment for The Drew Barrymore Show that aired on Thursday’s episode, Mathews was sent to Television City Studios to meet with a group of interns to discuss getting started within the entertainment industry. He was surprised mid-conversation by Leno, who drove up on a golf cart. 

“Oh my God, Jay Leno! Can I give you a hug?” Mathews gushed. “I haven’t seen you in so long!”

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After a quick hug, Leno told the interns, “Ross was my favorite intern. We had a lot of them, but he was the most annoying. That was the fun part.”

Mathews starting working on the The Tonight Show in 2001, rising to fame at first as an intern before becoming one of the show’s correspondents for events like the Academy Awards. “Can you believe, Jay, it’s been 23 years since I started on your show?” He asked. “And look at at us, we look great!” 

In response, Leno teased, “Well, I look great, anyway.” He then added, “No, no, you look good. You look terrific.”

The pair continued to reminisce about their days working together as they took a spin on the golf cart through the studio lot. “I cannot believe 23 years has gone by,” Mathews said. Leno appeared to feel the same way, replying, “I still think of you as a kid, but you’re like a grown adult now.”

To which Mathews joked, “I have a mortgage, Jay.” 

The Drew’s News cohost then explained that he “never had the chance” to tell Leno how much he learned from working on the show. 

“Well, we enjoyed having you. I always liked you because you were kind. I think you started in the mail room. I don’t mean this in a weird way, but you had no discernible talent,” he said as Mathews burst into laughter.

Leno then elaborated that most people that appeared on the show typically had an “act” that they would perform, like singing or dancing. “But you just had a funny personality,” he said. “I thought, ‘Well, this kid’s got something.’” 

The pair then reminisced over sending Mathews to the Ocean’s Eleven premiere. “I said, ‘Well, how about that new, annoying guy, Ross the intern?’ I think he might be funny,” He teased as Mathews laughed. “And you did a great job and then it kind of leap-frogged from there.”