When Olivia Rodrigo joined Billy Corgan on Friday night (7/31) at Lollapalooza, it became the 11th veteran star she has sung with.

The ever-generous 23-year-old has been happy to sing with musicians of all ages including those in her own generation (Addison Rae, Chappell Roan, Conan Gray), the vast majority of her guest appearances, thought, are with Gen X and Boomers.

Who can blame her for wanting to jam with living legends? Here are some highlights from those surprise duets.

Billy Joel (77)

On 8/24/22, Olivia joined the Piano Man at his favorite venue, Madison Square Garden for one of her songs “deja vu” and his only #1 in the UK, “Uptown Girl.”

When he introduced her to his audience Billy said, “She’s very talented and I like her music and so do my kids.”

David Byrne (74)

Last summer at the Governors Ball at Flushing Meadows, Queens, New York, 6/7/25, Olivia and Byrne did the classic Talking Heads tune, "Burning Down the House.”

The 1983 song was the only US Top 10 single the Talking Heads ever had.

Robert Smith (67)

A few weeks after singing with Byrne, Olivia appeared at the Glastonbury Festival on June 29 and found herself onstage with The Cure’s Robert Smith for “Friday I’m in Love” and “Just Like Heaven,” (whose Setlist History is mighty interesting).

Olivia ended up releasing their duet as a double single on last September with proceeds benefiting Doctors Without Borders, and included both songs on Live from Glastonbury (A BBC Recording).

Robert then became the very first featured artist on one of her records, when they recorded “What’s Wrong With Me” which they live debuted a few months ago during her surprise set at Primavera Sound in Barcelona.

The studio version of course is onYou Seem Pretty Sad for a Girl So in Love.

Sheryl Crow (64)

Nine time Grammy-winning Sheryl Crow joined Rodrigo for her hit “If It Makes You Happy” three times.

First at the Bluebird Café on 9/29/23, then at the Barclays Center on that November for her Rock & Roll Hall of Fame induction, then the following year during her GUTS tour at the Bridgestone Arena on 3/9/24.

Billy Corgan (59)

On Friday (7/31) Olivia returned to Lollapalooza and sang the sweet Smashing Pumpkins tune “Thirty-Three” with Billy Corgan.

A few days before, the Pumpkins dusted off the Mellon Collie and the Infinite Sadness gem the same night they had Greg Brady join them on stage. Apparently that run-thru of "Thirty-Three" was a warm up for his duet with Olivia.

Rivers Cuomo (56)

You may remember last year (8/1/25) when she headlined Lollapalooza she brought out Rivers Cuomo and Weezer for a pair of Blue Album bangers, “Buddy Holly” and “Say It Ain’t So.”

That day we learned Weezer was her very first concert as a fan and has loved them ever since.

Gwen Stefani (56)

For some mysterious reason Olivia has never done a full set at Coachella. Could next year finally be the year?

She's appeared twice as someone else's guest, this year she popped on with Addison Rae where she live debuted "drop dead."

But the first time she jump on stage in Indio was alongside Gwen and No Doubt on 4/13/24 where they rocked “Bathwater.”

Jewel, 52

On the fourth night of her MSG residency during the GUTS tour (4/9/24), Jewel and Olivia put on beautiful acoustic guitars and sang "You Were Meant For Me," a tune that peaked at #2 in 1996.

When Olivia introduced Jewel to the stage, she said, "She is such an incredible songwriter. When I first started writing my songs, I would listen to her album Pieces of You before I went to bed."

Alanis Morissette, 52

“This is probably the favorite night of my whole life, thank you guys for coming,” Rodrigo said on May 24, 2022, when she was just 19 years old.

She was playing the Greek Theatre in Los Angeles a place she would drive by and say she would play one day. Not only did that day come but she got to bang out “You Oughta Know” with Alanis under the stars in Griffith Park.

Natalie Imbruglia, 51

During that same Sour Tour, on July 6, 2022, Olivia had Natalie Imbruglia join her at the Eventim Apollo in London.

“I think she’s the most fantastic artist, the most fantastic singer," Olivia said about Natalie before bringing her out. "She sings one of my favorite songs of all time.”

Feist, 50

On 11/8/25 at the Peacock Theater at LA Live for the White Stripes' induction into the Rock & Roll Hall of Fame induction, Olivia and Feist sang one of the Detroit duo's sweetest songs, "We're Going to Be Friends."

Afterwards Olivia wrote on her IG, "I had a White Stripes fan account when I was 13 and last night I got to help induct them into the Rock & Roll Hall of Fame!!!!! What a surreal honour to sing one of their beautiful songs with the wildly talented Feist and celebrate music that means so much to me."

Later this month Feist plays a pair of shows at Red Rocks with LCD Soundsystem. Then she'll be at the Just Like Heaven Festival in Pasadena. Get your tix on her website.