Jay Leno Reunites with 'The Intern' Ross Matthews 23 Years After “Tonight Show ”Breakout

Leno admitted Matthews was his "favorite" intern because "he was the most annoying"

Ross "The Intern" Matthews finally got to show Jay Leno what he's worth.

The Sept. 12 episode of The Drew Barrymore Show brought a sweet reunion for the former The Tonight Show with Jay Leno intern, Matthews, now 44, and his former boss as Leno surprised Matthews on Television City Studios.

"Ross, how are you?" Leno said as he pulled up in a golf cart and shocked his former intern, who he joked "got your money's worth on that haircut."

"Oh my God, Jay Leno!" Matthews said as he went in for a hug. "Can I give you a hug? I haven't seen you in so long."

Leno told the interns Matthews had been talking to that he "was my favorite intern."

"We had a lot of them, but he was the most annoying," Leno quipped.

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"Can you believe it's been 23 years since I started on your show?" Matthews asked. "Look at us — we look great,"

"Well, I look great," Leno said, prompting Matthews, who now co-hosts Drew Barrymore's talk show with her, to tell him, "You've gotta give me your doctor's number."

On a more serious note, Leno told Matthews he looks "terrific." (Matthews has spoken about maintaining his 60 lb. weight loss over the last three years.)

The former co-workers then took a ride through the lot and a trip down memory lane as Leno admitted, "I still think of you as a kid but you're like a grown adult now."

"Isn't that weird? I have a mortgage, Jay," Matthews said. "I've never had the chance to really tell you how much I reference what I learned from you."

Leno said the Tonight Show team "enjoyed having" him as an intern all those years ago, as he recalled, "I always liked you because you were kind."

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"I don't mean this in a weird way, but you had no discernable talent. I mean you didn't sing, you didn't dance," Leno recalled. "You just had a funny personality, so I was like, 'Well this kid's got something.'"

As the clip ended, Leno remembered suggesting that Matthews, whom he called "that new annoying guy," be sent as a Tonight Show correspondent to the Ocean's Eleven premiere in 2001, and he did a "great job" and it "kind of leap-frogged from there."

Matthews' stint as an intern for Leno jumpstarted his career in the business, and he went on to star as a panelist on Chelsea Handler's Chelsea Lately, became a judge on RuPaul's Drag Race and an E! correspondent.

He's been a co-host of The Drew Barrymore Show since its premiere in 2020 as part of the segment "Drew's News."

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