The singer, who rose to fame as Ashlee Simpson's boyfriend on her MTV reality series, takes us inside the success of his debut single.
Ryan Cabrera
Credit: J. Countess/WireImage

The Throwback is a recurring column where we deep dive into hit songs from years past.

ARTIST: Ryan Cabrera

SONG: "On the Way Down"

CHART HISTORY: Peaked at No. 15 on the Billboard Hot 100 and No. 4 on the TRL chart.

LEGACY: Making big hair... cool?

WHERE ARE THEY NOW?: Currently working on new music as well as writing for other artists — including Avril Lavigne on her last record and upcoming South African artist Stefan Benz — and raising money for Camp Ronald McDonald with online concerts.

Picture the scene: It’s 2004. You’re wearing your super low-rise jeans and driving home from school a little faster than you should (lest you miss the start of TRL) when that song that plays on your local radio station 700 times a day comes on. It’s by that boy with the guitar and really big hair who dates Ashlee Simpson. You’re listening to Ryan Cabrera’s “On the Way Down” and you know all the words.

On June 12, 2004, Cabrera released “On the Way Down” and from then on you heard it nonstop all summer long. A simple pop-rock bop with sweet lyrics and a catchy chorus, the track was the reason the then 21-year-old singer-songwriter landed a record deal. Up until he penned that single, Cabrera had been struggling to be seen or heard in the music industry, showing up at every major record label with his acoustic guitar in the hopes of impressing. “I was getting turned down by every label across the board,” he tells EW. “Everyone said the same: 'We love your voice; we love your sound; your look, but we don’t hear a hit song, so no.’” After spending a stint in New York writing as much music as he possibly could all day, every day, Cabrera finally came up with “On the Way Down.” “Then one of the labels that had originally turned me down called and was like, ‘We always loved you! We knew you could do it,’” says Cabrera. “That was the spark. Because of that song, I got a record deal and that kicked off everything.”

Still, it wasn’t overnight success for the Texas-born singer. Despite a record deal with Atlantic Records and an album in the works, “On the Way Down” took a while to make its way up the charts. “When you’re new in the business, you expect things to happen quickly,” says Cabrera. “It debuted at like 198 and then the next week it was at 197, then 195, so I decided I was just going to play as many shows as possible. Any show I could get — Mexican restaurants, sorority living rooms. I was knocking on doors every day and being like, ‘Can I play for you?’ But that was what led 'On the Way Down' to last so long, because it was such a slow riser. Over months and months, it kept rising.”

It eventually peaked at No. 15 on the Billboard Hot 100 but reached No. 4 on MTV’s Total Request Live chart — meaning teen visibility was high. Cabrera’s first-ever appearance on the show is one of his standout memories from that period in his life. As was customary on the MTV series, artists performed in the New York City studio, overlooking a crowd in Times Square below. Upon arrival at the midtown studios, Cabrera didn’t like the idea of performing so far away from his fans. “There were thousands of people down there and they’d made signs,” he says. “So, I asked production if I could perform on the street with them. They started freaking out, but they did it! I did 'On the Way Down' for the first time in the middle of the Times Square crowd. No security. We just plopped that microphone in the middle and they wired it up to the studio upstairs so the band could hear it. That was definitely a cool moment — they probably thought I was nuts.”

Of course, you don’t get invited to MTV’s video chart show without a pretty popular music video in tow. For the “On the Way Down” video, Cabrera headed back to his native Texas (though Austin, not Dallas where he grew up), paying his dues by shooting in one of the bars he and his band Rubix Groove had frequented when they were trying to break through. “We rented out the spot where I’d played millions of times for nobody — literally just the bartenders clapping,” he says. “I paid my respects and we filmed the live scenes in there and I got my buddies to be the backup band. At the time, Ashlee [Simpson] and I were really good friends and living in the same house, so I asked her to be in the video. That video was actually what sparked our initial romance. I’m pretty sure we had our first kiss on camera.” The relationship with Simpson and her family didn’t hurt Cabrera’s record sales either. In the golden age of MTV reality television, he frequently appeared on his then girlfriend’s reality series The Ashlee Simpson Show in its second season and is even the subject of her debut single, “Pieces of Me.”

Ashlee Simpson and Ryan Cabrera
Credit: J. Merritt/FilmMagic

That Simpson family connection also landed Cabrera a spot on older sister Jessica’s tour, opening for the pop star, but his first on-the-road experience was working as a tech on early 2000s singer-songwriter Jewel’s circuit. “It was a great deal,” says Cabrera. “I just followed her around the country in a van. I’d do her soundcheck for her and then I got to open up. That’s where I initially started a bit of a grassroots fanbase and that’s what I thought my demographic was going to be. It was a little bit of an older crowd because those were sit-down, acoustic shows with Jewel and they were very receptive [to my music]. Then my next tour was a completely different experience and a completely different crowd.”

By the time Cabrera joined Simpson on the road for his next tour, fans had come to know him from his appearances on The Ashlee Simpson show as the titular character’s boyfriend, and “On the Way Down” was gaining some traction and airplay on the radio. But that didn’t stop Cabrera from devising a way to attract more attention. “I would sign 300 EPs and give them away after the show,” says the singer. “A lot of people were like, ‘Dude, you’re giving away your singles for free — that’s crazy,’ but I felt like they were going to appreciate it and want more.” Every night, before playing his final song, Cabrera would announce that he’d be giving away the 300 signed CDs at the back of the stadium right after he got off stage. “I would look up and the entire 30,000 thousand people would have just cleared out. It was mayhem. I thought it was so cool, but then no one was there to watch ‘On the Way Down.’ But I liked creating the pandemonium and I knew that those radio stations would look at that and go, ‘Oh, s---. What is this?’ The craziness of it made them go, ‘We gotta start playing this record.’” And they did.

Ryan Cabrera
Credit: Marc Andrew Deley/FilmMagic

Sixteen years later, “On the Way Down” is arguably the song Cabrera is still best known for — well, that, and his impressively high hair. “Doing it was a lot quicker process than people think,” he shares. “I would do my hair one day and it would take me 20 minutes, and I would wake up the next day and it would look the same. At that time, I was probably using Aquaphor because I couldn’t afford Bed Head yet and it would last for like three days. Kinda gross, but it worked. The number one fan request was always to touch the hair and I’d be like, ‘Be gentle!’”

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