All of Olivia Rodrigo's 'High School Musical' Songs From Season 1

Olivia Rodrigo
David Needleman

Olivia Rodrigo, Chanel vest and Thom Browne shirt.

Before 2021's biggest breakout hit "Drivers License" zoomed to the top of the Billboard Hot 100, Olivia Rodrigo was chugging along as part of the Disney machine while starring in High School Musical: The Musical: The Series.

The High School Musical-inspired series premiered on Disney+ in November 2019, more than a year before the release of "Drivers License" and before she could get her actual driver's license (Rodrigo said in an interview that her filming schedule actually caused her to cancel her second of four attempts to take her driver's test and pass). Even if the teen sensation took the longer route to finally get it, she took the fast lane to superstardom. Rodrigo's current Billboard cover story breaks down how she skipped the usual path of going to Disney-owned Hollywood Records that past Disney stars Miley Cyrus, Demi Lovato and Selena Gomez once took and went straight to a major label, Geffen Records.

"I've known a couple of the stars and knew which ones when I worked with I was thinking, 'Oh, this person's going to be a superstar.' It's ridiculous for me to say that Olivia is going to be a superstar because she is already a superstar," Mitch Allan, Disney Channel veteran songwriter and producer, previously told Billboard.

Before the second season of HSMTMTS premieres Friday on Disney+ and Rodrigo releases her debut full-length album Sour on May 21, Billboard is pumping the brakes and reversing through all the songs she performed on the first season. And watch HSMTMTS by signing up for Disney+ here.

"I Think I Kinda, You Know" (solo and with Joshua Bassett)

Rodrigo, who plays musical theater enthusiast Nini on HSMTMTS, surprises Ricky (Joshua Bassett) with a swoon-worthy, ukulele-driven song for their one-year anniversary, polished with her sweet vocals riffs on the outro: "Guess I'm sayin' I don't not love you." And the duet version makes "the way that we flow" that much sweeter.

"Start of Something New"

"Start of Something New" is recycled from the first High School Musical film from 2006, but Nini holds her ground on her own unlike the original Troy Bolton-Gabriella Montez duet and grounds her performance with her voice that's like a force of nature and started something major for Rodrigo's career.

"Wondering" with Julia Lester

Ashlyn (Julia Lester) performs the power ballad "Wondering" after being cast as Ms. Darbus, writing from her perspective of a high school drama teacher who regrets not being the big star she always dreamed of being. Nini hops on, her reflection about not taking a chance and missing out on something great driving her to hit the high notes she breaks out once in a while for a special moment.

"What I've Been Looking For" with Matt Cornett

Nini and E.J. (Matt Cornett) dust off another HSM throwback jam -- which hit the Hot 100 twice in 2006, once for Ashley Tisdale and Lucas Grabeel's uptempo version (No. 35) and again for Zac Efron and Vanessa Hudgens' slower reprise (No. 67). But these two give fans of the old franchise an ice-cold (and disjointed) taste of what's intended to be a heartfelt duet since the former couple ended their relationship right before starting rehearsals, with Rodrigo's sarcastic take and over-the-top outro packing an extra punch.

"All I Want"

Tim Federle, HSMTMTS creator and showrunner, told Billboard for Rodrigo's cover story that he realized he needed a song for Nini in the middle of the first season and tapped her to write it upon discovering the original songs she posted to Instagram. The result was "All I Want," a sweeping piano ballad about being repeatedly let down by boys from her past, which landed in the fourth episode and eventually landed her major record deal with Interscope. The song also ended up being Rodrigo's first entry on the Hot 100, peaking at No. 90 in January 2020. "Drivers License" propelled the HSM song to enter the Billboard Global 200 and Billboard Global Excl. U.S. tallies in January 2021.

"Bop to the Top" duet

Only 35 seconds long, Nini and Kourtney (Dara Reneé) breathe new life into the playful "Bop to the Top" from the original film while laying their vocals over Tisdale and Grabeel's. The song does not appear in the first season of the series but made it onto High School Musical: The Musical: The Series: The Soundtrack. 

"Out of the Old"

After Ashlyn convinces Nini to write a song about herself instead of her relationships, she looks inward, contemplating "Am I on the right road?" before belting out the chorus to "Out of the Old," an empowering anthem about what's stopping her from pursuing her dreams while wondering whether she could achieve them if she leaves her past in the rearview mirror.

"Just for a Moment" with Bassett

Rodrigo and Basset co-wrote "Just for a Moment" with music producer Dan Book, and their original duet serves as the confession of their love for one another and a nice precursor to their "Even When/ The Best Part" "accidental duet" that will be featured on the upcoming second season.

"Breaking Free" trio

While "Breaking Free" was originally a Troy and Gabriella duet, the series made the song fit for three characters -- Nini, Ricky and E.J. -- who were embroiled in a love triangle in the series. E.J., who was playing Troy's understudy for Ricky after he abruptly left midway through the musical, steps aside and lets him and Nini finish the performance together, which truly seals the fate of their love in the song's full-blown production.