15 Conan Gray Songs to Listen to on Repeat

Conan Gray wants you to stop sulking over your sh*tty ex. At 23, Gray has made a name for himself as an indie-pop icon, due in part to his luscious waves but mostly to his sentimental lyrics, which read like a stream of consciousness. His songs — a cross between bedroom pop and indie rock — range from dreamy to straight-up cynical and beautifully illustrate the complex emotions that stir up inside us after breakups, hookups, and everything in between.

"All of my friends and my fans know that I'm a cynical person," Gray told Apple Music ahead of the release of his debut album, "Kid Krow," in March 2020. "I had a dark enough past as a kid, and so in my teen years and adult years, I just kind of laugh at the things that go wrong in my life."

After starting his music career on YouTube in 2015, Gray self-released his debut single, "Idle Town," in March 2017. In February 2019, he went on to make his TV debut on "Late Night With Seth Meyers." He's since taken home the 2019 Shorty Award for best YouTube musician, and he was nominated for a People's Choice Award for best new artist in 2020. His most popular songs to date include "Heather," a reflective song about envy, and "Maniac," lyrical hate mail to an ex who refused to leave him alone.

Equipped with a discography full of cathartic songs that touch on romantic confusion, loneliness, and raw anger, it's no surprise that Gray is friends with other singer-songwriters like The Kid LAROI and Olivia Rodrigo, whose "Good 4 U" has become a pop-punk heartbreak anthem. Whether Gray has any plans to collaborate with his friends or other artists on his upcoming album, "Superache," remains a mystery.

Ahead of the release of Gray's sophomore album on June 24, check out his best songs here.

click to play video

"Maniac" by Conan Gray

Gray wrote "Maniac," a "cathartic post break-up song dedicated to psychotic exes," after receiving a drunk text from his ex at midnight. "I wrote maniac in the shower after getting a midnight drunk sob text from my ex," he told Universal Music Group. "They'd been running all around town telling everyone that I was some freak who wouldn't leave them alone when in reality, they were the freak. They were the one acting like a maniac — sending strange late-night texts and showing up at my shows unannounced."

In the music video, Gray and "The End of the F***ing World" star Jessica Barden team up during a night shift at a cinema to fight off her ex-boyfriends, who've risen from the dead. Watch the video and listen to "Maniac" here.

click to play video

"Heather" by Conan Gray

"Heather" is the sixth single off of Gray's debut album, "Kid Krow," released in 2020. Speaking with James Corden on "The Late Late Show" in October 2020, Gray said he was initially hesitant to release the song because he was "embarrassed" and didn't think anyone would relate to it. "'Heather' is the song on the album that I always cry to," he told Apple Music. "I think it's the most honest recount of my love life at the moment. It's about a girl named Heather — I think everyone has a Heather in their life. The person that I really, really liked was in love with Heather. They were not in love with me, and because of that, I f*cking hated Heather. I hated Heather with all of my heart and soul."

Commenting on the complex emotions he was feeling toward Heather, Gray continued, "I had no reason to hate Heather. Heather is a perfectly nice girl. She's sweet and she's pure and she smells like daisies — she's perfect, but I hate her. It's this humiliating thing to admit, but it's just true. I'm scared to see how people are going to react, because it isn't a good thing to think something like that, but I also think it's something that I've never really heard anyone admit. I'm sorry, Heather. You're a wonderful person."

Watch the "Heather" video here.

click to play video

"Wish You Were Sober" by Conan Gray

Gray wrote "Wish You Were Here" about a love interest who would only admit they liked him when they were drunk. "It was a weird, bittersweet feeling, because on one side you're thinking, 'Yay, they like me and they have feelings for me and they like me back," he told Apple Music. "On the other side you're thinking, 'Why can't you tell me this when you're sober? Why can't you tell me this in daylight?' I think the song is about all those mixed emotions and all the craziness behind being young and getting super drunk and calling someone and telling them that you love them."

Watch the full "Wish You Were Sober" video here.

click to play video

"People Watching" by Conan Gray

"People Watching" is a song about loneliness and the bittersweet feeling attached to seeing other couples in love. The song, which was released on July 14, 2021, is rumored to be a single off of Gray's upcoming album.

Watch the "People Watching" video here.

click to play video

"Memories" by Conan Gray

Conan's newest single, "Memories," is about trying to move on from a bad relationship when the other person insists on being friends and staying in your life. The video features Gray at home alone, reminiscing about his past relationship as he looks through boxes of mementos and tries to move on from the sour romance.

Watch the full "Memories" video here.

click to play video

"Comfort Crowd" by Conan Gray

After making the move from his small hometown, Georgetown, TX, to Los Angeles to attend UCLA, Gray was overwhelmed by feelings of loneliness and came up with the song as he reminisced about the good times he longed for with his friends back home. "It was a total realignment of who I was, everything that I wasn't used to," he told Apple Music. "I was so homesick and I missed my friends back home so much. They're the ones who keep me sane, so I just wanted to be with them and hang out with them the way we used to. We would just sit around on the couch and show each other stupid things on our phones and enjoy each other's company without even having to talk at all."

Watch the full "Comfort Crowd" video here.

click to play video

"Idle Town" by Conan Gray

"Idle Town" is the first track on Gray's "Sunset Season" EP. According to the description on the music video, which features Gray singing into a water bottle as he runs through his hometown, the song is "a tribute to my senior year of highschool; for my friends, my town, my homes, and my memories."

Watch the heartwarming "Idle Town" video here.

click to play video

"Generation Why" by Conan Gray

"Generation Why" is one of the biggest hits on Gray's debut studio EP in 2018. The song's title is a play on Generation Y, a nickname for people born between 1975 and 1985. The song itself focuses more on Gen Z and people in their 20s, illustrating how the media portrays the younger generation as selfish and aimless.

Watch Gray's "Generation Why" video here.

click to play video

"The Story" by Conan Gray

"The Story" is the fourth single from Gray's "Kid Krow" album and tells the story of his childhood, a painful time in his life that he reflects on often.

"I had a pretty rough childhood; a lot of it was just really unsafe," Gray told Apple Music. "There were times as a kid that I wished so badly that I just didn't exist anymore. I wanted so badly for my pain to stop, and I wanted to just stop existing. Every single time that I would hit those rock-bottom moments, something would just tell me to keep going. . . . with the smallest amount of courage — and with people who can show you that they love you — you can keep going and it's never really the end."

Watch the full video for "The Story" here.

click to play video

"Fake" by Lauv and Conan Gray

Gray collaborated with Lauv in October 2020 to release "Fake," a song calling out people who present inauthentic versions of themselves for attention. "Yeah, we were literally just ranting. It was barely writing a song," Gray told Paper Magazine about his first collaboration. "We were just talking and ranting about weird-ass people, who are just fake. I feel like there's so much bullsh*t when it comes to like, friends and relationships, especially as you get older. It gets so complicated. When you're a kid, you can just go up to someone and be like, 'Can you be my best friend?' and you'll literally be best friends for the rest of your life. It's like, the older you get, it gets so complicated with all this drama. It gets so confusing."

Watch the full video for "Fake" here.

click to play video

"Astronomy" by Conan Gray

A hidden gem in Gray's discography, "Astronomy" is the first prereleased single expected to appear on his upcoming album. The song touches on the heartbreak of realizing you've grown apart from someone you once loved and that you're no longer the same people you used to be. In the video, Gray reflects on these feelings during a long drive through the desert at dusk.

Watch the full "Astronomy" video here.

click to play video

"Overdrive" by Conan Gray

Gray's song "Overdrive" is about diving headfirst into a relationship as soon as you realize you like somebody. The lyrics touch on the risk associated with going all in on a romance so quickly and the thrill of finding someone who you never want to be without. In the video, Gray lets loose, going out for a night on the town that results in a healing drive down the highway à la "The Perks of Being a Wallflower."

Watch the "Overdrive" video here.

click to play video

"Crush Culture" by Conan Gray

"Crush Culture" appeared as the second single on Gray's debut EP, "Sunset Season." The song is inspired by his desire for a romantic relationship and the bitterness he felt at seeing happy couples all over his high school. During a "Sidewalk Talk" with Lauren Engel, Gray explains that the song "came out of this spot of bitterness. I think everyone who's single kinda looks at people who are in love and you kinda wanna be happy for them but you're more just kinda like 'God, like y'all are so disgustingly in love. I wanna be you but I can't, so I'm just gonna beat you up."

Watch the full "Crush Culture" video — which features Gray taking a baseball bat to his emotions — here.

click to play video

"Lookalike" by Conan Gray

Also from Gray's "Sunset Season" EP, "Lookalike" is a song about lingering feelings of love. According to Gray, the song is about that one person who sticks in your mind even after you've fallen in love with other people, who you look for pieces of in everyone else you meet, and who you can't get out of your mind no matter how much time has passed.

Listen to "Lookalike" here.

click to play video

"Telepath" by Conan Gray

A must have on any Conan Gray playlist, "Telepath," which is expected to appear on his upcoming sophomore album, is a song about being jaded by indecisive exes who toy with his emotions, insisting they want to break up before they come crawling right back.

Listen to "Telepath" here.