Jay Leno Reunites with 'The Intern' Ross Mathews 23 Years AfterTonight ShowBreakout

Mar. 15, 2025

Jay Leno (left); Ross Matthews.Photo:Weiss Eubanks/NBCUniversal via Getty; Gail Schulman/CBS via GettyRoss “The Intern” Mathewsfinally got to showJay Lenowhat he’s worth.The Sept. 12 episode ofThe Drew Barrymore Showbrought a sweet reunion for the formerThe Tonight Show with Jay Lenointern, Matthews, now 44, and his former boss as Leno surprised Mathews 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!” Mathews 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 Mathews had been talking to that he “was my favorite intern.““We had a lot of them, but he was the most annoying,” Leno quipped.“Can you believe it’s been 23 years since I started on your show?” Mathews asked. “Look at us — we look great,““Well, I look great,” Leno said, prompting Mathews, who now co-hostsDrew 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 Mathews he looks “terrific.” (Mathews has spoken about maintaininghis 60 lb. weight lossover 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,” Mathews said. “I’ve never had the chance to really tell you how much I reference what I learned from you.“Leno said theTonight Showteam “enjoyed having” him as an intern all those years ago, as he recalled, “I always liked you because you were kind.“Ross ‘the intern’ Matthews on ‘The Tonight Show with Jay Leno’ on May 22, 2009.Margaret Norton/NBCU Photo Bank"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 Mathews, whom he called “that new annoying guy,” be sent as aTonight Showcorrespondent to theOcean’s Elevenpremiere in 2001, and he did a “great job” and it “kind of leap-frogged from there.“Drew Barrymore, Jay Leno and Ross Matthews on ‘The Drew Barrymore Show’.The Drew Barrymore ShowMathews’ stint as an intern for Leno jumpstarted his career in the business, and he went on to star as a panelist onChelsea Handler’sChelsea Lately, became a judge onRuPaul’s Drag Raceand an E! correspondent.He’s been a co-host ofThe Drew Barrymore Showsince its premiere in 2020 as part of the segment “Drew’s News.“Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.The Drew Barrymore Showairs weekdays. Check local listings.

Jay Leno (left); Ross Matthews.Photo:Weiss Eubanks/NBCUniversal via Getty; Gail Schulman/CBS via Getty

Weiss Eubanks/NBCUniversal via Getty; Gail Schulman/CBS via Getty

Ross “The Intern” Mathewsfinally got to showJay Lenowhat he’s worth.The Sept. 12 episode ofThe Drew Barrymore Showbrought a sweet reunion for the formerThe Tonight Show with Jay Lenointern, Matthews, now 44, and his former boss as Leno surprised Mathews 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!” Mathews 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 Mathews had been talking to that he “was my favorite intern.““We had a lot of them, but he was the most annoying,” Leno quipped.“Can you believe it’s been 23 years since I started on your show?” Mathews asked. “Look at us — we look great,““Well, I look great,” Leno said, prompting Mathews, who now co-hostsDrew 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 Mathews he looks “terrific.” (Mathews has spoken about maintaininghis 60 lb. weight lossover 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,” Mathews said. “I’ve never had the chance to really tell you how much I reference what I learned from you.“Leno said theTonight Showteam “enjoyed having” him as an intern all those years ago, as he recalled, “I always liked you because you were kind.“Ross ‘the intern’ Matthews on ‘The Tonight Show with Jay Leno’ on May 22, 2009.Margaret Norton/NBCU Photo Bank"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 Mathews, whom he called “that new annoying guy,” be sent as aTonight Showcorrespondent to theOcean’s Elevenpremiere in 2001, and he did a “great job” and it “kind of leap-frogged from there.“Drew Barrymore, Jay Leno and Ross Matthews on ‘The Drew Barrymore Show’.The Drew Barrymore ShowMathews’ stint as an intern for Leno jumpstarted his career in the business, and he went on to star as a panelist onChelsea Handler’sChelsea Lately, became a judge onRuPaul’s Drag Raceand an E! correspondent.He’s been a co-host ofThe Drew Barrymore Showsince its premiere in 2020 as part of the segment “Drew’s News.“Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.The Drew Barrymore Showairs weekdays. Check local listings.

Ross “The Intern” Mathewsfinally got to showJay Lenowhat he’s worth.

The Sept. 12 episode ofThe Drew Barrymore Showbrought a sweet reunion for the formerThe Tonight Show with Jay Lenointern, Matthews, now 44, and his former boss as Leno surprised Mathews 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!” Mathews 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 Mathews had been talking to that he “was my favorite intern.”

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

“Can you believe it’s been 23 years since I started on your show?” Mathews asked. “Look at us — we look great,”

“Well, I look great,” Leno said, prompting Mathews, who now co-hostsDrew 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 Mathews he looks “terrific.” (Mathews has spoken about maintaininghis 60 lb. weight lossover 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,” Mathews said. “I’ve never had the chance to really tell you how much I reference what I learned from you.”

Leno said theTonight Showteam “enjoyed having” him as an intern all those years ago, as he recalled, “I always liked you because you were kind.”

Ross ‘the intern’ Matthews on ‘The Tonight Show with Jay Leno’ on May 22, 2009.Margaret Norton/NBCU Photo Bank

Margaret Norton/NBCU Photo Bank

“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 Mathews, whom he called “that new annoying guy,” be sent as aTonight Showcorrespondent to theOcean’s Elevenpremiere in 2001, and he did a “great job” and it “kind of leap-frogged from there.”

Drew Barrymore, Jay Leno and Ross Matthews on ‘The Drew Barrymore Show’.The Drew Barrymore Show

The Drew Barrymore Show

Mathews’ stint as an intern for Leno jumpstarted his career in the business, and he went on to star as a panelist onChelsea Handler’sChelsea Lately, became a judge onRuPaul’s Drag Raceand an E! correspondent.

He’s been a co-host ofThe Drew Barrymore Showsince its premiere in 2020 as part of the segment “Drew’s News.”

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.

The Drew Barrymore Showairs weekdays. Check local listings.

source: people.com