12/01/2025
Ryan Cabrera is fully cheering on ex-girlfriend Ashlee Simpson as she steps back into the spotlight — and he’s eager to see her upcoming Las Vegas shows for himself.
“Everybody’s excited about it. All my friends are messaging me like, ‘Hey, I’m going to Vegas — can we go see Ashlee?’ And I’m like, ‘Dude, I would love to see that show.’ Even my wife wants to go,” Cabrera, 43, told Us Weekly while celebrating the 20th anniversary of “On the Way Down.” “I even messaged Tina [Simpson] when I saw the news, and it made me want to revisit those albums again.”
Cabrera and Simpson, 41, dated in 2004 and famously documented their early careers on MTV’s The Ashlee Simpson Show. That same year, Simpson also starred in Cabrera’s “On the Way Down” music video.
Though both have married other people — Cabrera to WWE star Alexa Bliss and Simpson to Evan Ross — the respect between them remains strong.
“Ashlee was always an incredible performer,” Cabrera said. “She stepped back to be a mom and a wife, but now she’s got the bug again. It’s time for her to get back on stage and let those creative juices flow. From what I’ve heard, she’s crushing it. I haven’t seen the show yet, but I want to. And she should be doing more — touring, making new music — all of it.”
Simpson recently announced that her I Am Me shows at Voltaire at The Venetian Resort will return for two more weekends in January 2025.
“I think she influenced a lot of the female artists coming up today,” Cabrera added. “I bet she’ll do some collaborations next year — and they’re going to be fire. I wish nothing but the best for everyone over there.”
As Simpson revives her biggest hits, Cabrera is celebrating a milestone of his own. For the 20th anniversary of “On the Way Down,” he teamed up with AJ McLean of Backstreet Boys, Joey Fatone of *NSYNC, Drake Bell, Walk the Moon’s Nick Petricca, Taylor Hanson, and Nash Overstreet for a star-studded collaboration.
“We put together a team — boy band legends, rock stars, emo guys. It was this wild mix of artistry, and they made the song what it is,” Cabrera explained. “I remember telling them, ‘Don’t do what you’ve heard. Don’t do what I did. Do your thing.’ And I think they had fun with it.”
Two decades later, Cabrera — now married and a dad — is still performing across the country.
“We’re continuing the Pop 2000 Tour, which goes into year eight next year,” he said. “As long as people keep showing up, we’re not going to stop playing.”