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.

Ryan Cabrera

Credit: J. Countess/WireImage

4 on the TRL chart.

LEGACY:Making big hair… cool?

WHERE ARE THEY NOW?

Ashlee Simpson and Ryan Cabrera

J. Merritt/FilmMagic

Picture the scene: It’s 2004.

It’s by that boy with the guitar and really big hair who datesAshlee Simpson.

You’re listening to Ryan Cabrera’s “On the Way Down” and you know all the words.

Ryan Cabrera

Marc Andrew Deley/FilmMagic

“I was getting turned down by every label across the board,” he tells EW.

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 an overnight success for the Texas-born singer.

“When you’re new in the business, you expect things to happen quickly,” says Cabrera.

Any show I could getMexican restaurants, sorority living rooms.

I was knocking on doors every day and being like, ‘Can I play for you?’

Over months and months, it kept rising."

It eventually peaked at No.

15 on the Billboard Hot 100 but reached No.

4 on MTV’sTotal Request Livechartmeaning teen visibility was high.

Cabrera’s first-ever appearance on the show is one of his standout memories from that period in his life.

“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.

That was definitely a cool momentthey probably thought I was nuts.”

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.

“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.

Then my next tour was a completely different experience and a completely different crowd.”

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.

“I would look up and the entire 30,000 thousand people would have just cleared out.

What is this?'

The craziness of it made them go, ‘We gotta start playing this record.'”

“Doing it was a lot quicker process than people think,” he shares.

Kinda gross, but it worked.