Olivia Rodrigo and Conan Gray's Friendship Deserves Its Own Grammy-Winning Album

Olivia Rodrigo and Conan Gray are two of music's biggest stars thanks to their killer songwriting chops—and they just so happen to be best friends, too. The pair initially met on the internet "just like everyone else our age," according to Conan, and openly mused about their love for Taylor Swift on their social timelines. Since then, Liv and Conan have danced at awards shows together, taken vacays with their besties Iris Apatow and Madison Hu, and even sparked collaboration rumors. Now, if that's not a friendship worthy of a Grammy-nominated album, I don't know what is. 🥹

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Ready to revisit the best moments of Olivia Rodrigo and Conan Gray's friendship timeline? Go back to the beginning with all the details below.

Circa 2020

Olivia wrote and performed "All I Want" for High School Musical: The Musical: The Series, and the track eventually went viral on TikTok. In a June 2022 interview on The Today Show, Conan revealed that his friendship with Liv started via DM when he first heard it.

"I remember I messaged her because I heard a song she'd written years ago called 'All I Want' and I was like, 'That's the best song I've heard in a very long time,'" he told host Hoda Katb.

March 26, 2021

Olivia and Conan were some of the few lucky folks who got an advanced stream of Fearless (Taylor's Version) and Liv posted this *very real* account of their experience:

April 8, 2021

Speaking of Tay's Fearless re-record, the Grammy winner enlisted Olivia and Conan to post a promotional video ahead of its drop on April 9. The duo paid homage to Taylor's music video for "You Belong With Me" with handwritten signs.

June 30, 2021

Olivia dropped her iconic Sour prom special, which featured Lydia Night, Conan, Madison, and Iris.

October 31, 2021

The duo attended a Halloween party, where they danced the night away as Elvira Hancock from Scarface and Rodrick from Diary of a Wimpy Kid.

November 22, 2021

Olivia attended her first American Music Awards, and ofc, her bestie Conan was her date for the evening.

December 3, 2021

"The girls r girling" with Conan, according to an O-Rod photo dump.

December 5, 2021

The "Traitor" singer posted birthday wishes for Conan on Instagram with an adorable message that'll make your heart swell. "happy birthday sweet cone. i love u more than anyone has loved anyone ever," she wrote.

January 1, 2022

Olivia and Conan rang in 2022 together, complete with top hats and party horns. 🥳

February 18, 2022

Liv, Conan, Iris, and The Kid Laroi had a fun-filled day at Disneyland. That roller coaster pic? Honestly, hang it in the Louvre.

February 20, 2022

Conan rang in Olivia's birthday with a carousel of pics, writing, "happy bday my liv <3 my heart has been looking for yours for a long long time. love u endlessly."

April 8, 2022

Liv and Conan recreated an iconic scene from Twilight during her Sour Tour stop in Vancouver (and, yes, I've been replaying this TikTok ever since):

Conan also came out as a special guest and *flawlessly* covered "The One That Got Away" by Katy Perry with Olivia. "ilysm @conangray singing with u is my favorite thing everrrr," Olivia wrote on Instagram.

May 1, 2022

Ahem, a moment of silence for the duo's slay at the Met Gala:

Liv and Conan also hit up Carbone in NYC after the coveted event.

June 17, 2022

Conan gushed about his friendship with Olivia in conversation with Rolling Stone, saying, "I very much value quality over quantity in my life. With Olivia, she's someone that I just adore. And it's always nice to have friends that you can depend on. [Fame] is a very confusing thing, and it's nice to have people that you can relate to and find comfort in."

June 24, 2022

Conan dropped his sophomore album, Superache, featuring a song called "Best Friend." Fans theorized that the track was partly inspired by his friendship with Olivia with lyrics like:

Not! To! Mention! The official lyric video is formatted to look like Instagram DMs, which is how the duo initially connected in 2020. S'cute!

July 1, 2022

While fans began theorizing (and manifesting) a musical collaboration between Conan and Olivia, he put rumors to rest during an interview with PopBuzz. The main theory at the time was that they wrote a track called "Dreamlike" together. "People love to make things up and then nobody cares, on the internet, if something is true or not," Conan explained. "That song doesn't exist. I'm sorry to let people down."

July 23, 2022

Olivia, Conan, and Madison had a chill beach day in Malibu.

October 22, 2022

Olivia, Madison, and Iris pulled up in chic DIY shirts to support Conan during his Superache Tour. Olivia's shirt referenced the lyrics to his track "Best Friend."

November 21, 2022

BLACKPINK was very much in Conan, Olivia, and Iris' area, per this adorable photo dump on Conan's Insta:

February 5, 2023

Conan and Olivia hit up Universal Music Group's Grammys after party at Milk Studios in LA.

February 21, 2023

Excuse me as I 🥹🥹🥹 at Conan's sweet message for Olivia's 20th birthday.

May 1, 2023

The pair attended the Met Gala and its respective after-parties. Allow me to present alllll the content that came from the first Monday in May:

July 3, 2023

Olivia released "Vampire," the lead single for her album GUTS and celebrated with a cute Instagram post. Conan showed his support in the comments, writing, "i, dare say, streamed ☝️😌."

July 11, 2023

Another day, another photo dump. This time, Conan posed with a promotional pic of Olivia out in the wild.

November 13, 2023

The pair posed for cute pics at the premiere of The Hunger Games: The Ballad of Songbirds and Snakes.

November 16, 2023

The duo attended a VIP dinner for GQ's Men of the Year Party at the Chateau Marmont in LA, and Olivia posted a 🔥🔥🔥 polaroid with Conan on Instagram.

November 20, 2023

"Konin" and Liv took London (and she left a cheeky comment on his post)!

December 2, 2023

Conan and Olivia posed together in matching florals at Variety's Hitmakers brunch.

December 8, 2023

Conan, Madison, and Iris hung out with Olivia's boyfriend Louis Partridge and watched her set at iHeart Radio's Jingle Ball in New York.

January 26, 2024

Conan enlisted Olivia and another friend to help tease his third album, Found Heaven. The trio posed by holding up "1-3-1" with their fingers, and the "Heather" hitmaker announced Found Heaven on January 31.

April 3, 2024

Conan sang some of Olivia's songs during a livestream with fans (he's just like me, for real).

April 5, 2024

During an interview, Conan revealed that "All-American Bitch" and "Lacy" are some of his favorite songs by Olivia. He also dished that they "bonded" over his 2019 track, "Lookalike."

April 7, 2024

Conan, Olivia, and Madison were out and about in NYC's West Village.

April 9, 2024

Conan attended Olivia's GUTS Tour at Madison Square Garden, where he fully jammed out with Joe Locke and Kaia Gerber.

The crew also attended an after party, according to fan accounts.

April 10, 2024

Olivia and Conan were spotted taking a stroll in the Greenwich Village after her Guts Tour in NYC.

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