Ryan Cabrera and Ashlee Simpson: A Look at His Reality TV Exes

Sometimes I lie awake at night not sure exactly how Ryan Cabrera entered my life, all our lives, really. I can recall sick days stuck watching The Ashlee Simpson Show with this strange, porcupine-haired creature in the background, and then hazy memories of him popping up in those formative days of reality television. But what really mystifies me is how he got famous in the first place, and how he, of all people, ended up cameo-ing in every other teen show, lurking on every other reality TV hottie.

Because it’s not like he has the famous relations or classically douchey hotness of one Brody Jenner, someone who also made similar television rounds. Understanding how the 35-year-old slipped onto our screens is a more nuanced process. So we’re going to break down, piece by piece, how Ryan Cabera ended in so many reality TV shows

Who even is Ryan Cabrera?

Sparknotes version: Ryan is originally a Texas boy who had humble beginnings as the lead singer of the band Rubix Groove. He released an independent solo record in 2001 and then followed it up with Take It All Away. In 2004, he released the smash hit single “On The Way Down” (still a banger) and probably other songs, but I didn’t listen to them, and you probably didn’t listen to them either.

Now, let’s move on to his television career.

The Ashlee Simpson Show

Ryan was prominently featured on The Ashlee Simpson Show for one obvious reason and one stealth reason: he was dating the star, Ashlee Simpson, and was managed by her father Joe Simpson. He lived with the Simpsons for eight months and became a part of their everyday adventures. It was an innocent time.

“Ashlee’s show was 100 percent real,” he later relayed in 2016. “They just followed us around. TV shows at that time were completely different. They literally just followed you around with a camera and whatever happened, happened.”

To be fair, Ashlee and her old nose seemed to be very in love with Ryan and vice versa. In addition to the show and her role in the “On The Way Down” vid, the two still seem to be friendly today. But of course, all good things must come to pass — and while Ashlee’s biggest move was to Pete Wentz-ier pastures, Ryan headed for…

The Hills

After taking up relationships with one of The Veronicas (so late-2000s it hurts) and Riley Keough, Ryan got a new reality TV star girlfriend: Audrina Patridge. The 32-year-old beauty was dating Ryan and busy holding together The Hills in a post-Lauren Conrad world. Subsequently, their romance became a plot point in the show’s final season.

Ryan insists that while his relationship was real off-camera, the pair had to fabricate things to keep the plot going… even after their breakup. Audrina admitted that they kept up the boyfriend-girlfriend facade during his Wango Tango performance just because they were filming.

“I had to stand there and watch him sing,” she confessed in a 2010 Regis & Kelly interview. “I started crying at the show.”

Dark.

The weird part about all of this, however, is that Ryan insisted that in retrospect, he didn’t really want any part of The Hills life. “For me, I wasn’t really wanting to be on that show,” he said. “It just so happened my girlfriend was on the show at the time, and they wanted to film and I was just like whatever.”

Ok, Ryan, but considering just how orchestrated The Hills seemed to be, it doesn’t feel like a “whatever” decision. Instead, it feels more like you signed up to play the role of Ryan Cabrera. But the most egregious cameo is still to come…

Pretty Wild

Pretty Wild isa cult favorite when it comes to the reality TV genre. For those who missed the 10 episode train wreck in it’s first run, it mainly followed IRL Bling Ring member Alexis Neiers. It also features this iconic phone call, which should be watched 20 times a day.

But whatever — Ryan Cabrera.

Ryan appears on an episode of the show where he gives Tess Taylor a private (except for the video cameras) music lesson (literally shows her how to play three keys). They then go on the most painful non-date of all time, which involves bowling and Ryan brings a friend and everyone watching it feels very uncomfortable.

SO. By the time Ryan has his weird episode in Pretty Wild I start to put my conspiracy theory cap on, because that is ri-goddamn-diciulous. First of all — for reasons too extensive and dark to embellish here — Pretty Wild was basically a very elaborate work of fiction. But independent of that, it seems so weirdly specific and contrived that Ryan would end up with this featured stint.

If he got wrangled into The Ashlee Simpson Show because of his managerial obligations to Joe and his relationship with its titular star, cool. If he got bullied into doing The Hills because he was with Audrina, I sort of buy it. But Pretty Wild? Legit, not-even-an-MTV show Pretty Wild?

DO NOT SIT HERE. AND ACT LIKE YOU WEREN’T CLAWING AT FAME. LIKE, I DON’T CARE. BUT THAT IS SOMETHING YOU ACTIVELY AGREED TO. COME. THE HELL. ON.

Anyway, let me wrap this up.

Conclusion: I Don’t Get It

While Ryan has since divorced from television, it would seem like he’s still out there doing music; he released an EP titled Wake Up Beautiful in 2015 and in 2016 he released a single with his new collaborative Beyond the Sky. Genuinely, I wish him the best.