Kid Cudi is one of the most out-there and genuine hip-hop artists we have ever seen. Never afraid to make his music deeply personal and dive into issues that most other hip-hop artists would never touch, mental health included, he’s been one of the best artists out there since his debut studio release in 2008. In this article, we’ll be going over 21 of Kid Cudi’s best songs (at least so far).
1. Pursuit of Happiness
It might have been the third single from his debut album, but Pursuit of Happiness is hard to argue against as Kid Cudi’s best song. You might think the title is a positive one, like pursuing happiness in life and making progress in your career, but you’d be wrong.
It weaves a tale of escapism, discussing the consequences of drinking and driving and the pain caused by drug addiction. The song bounced around the charts, entering and reentering a few times, but peaking in the US at number 59. Pursuit of Happiness has sold over 10 million units as a single and was certified diamond by the RIAA in 2022.
Next: Greatest sad songs of all time (full list)
2. Mr. Rager
Mr. Rager is about a hip hop star who’s tired of reality and searches for thrills and stimulation by any means necessary. According to Cudi, he was in a dark place, angry at the world and flirting with death by cocaine overdose at the time he wrote it.
It’s honestly a deeply personal song for Cudi, a reminder of a dark time in his life when he struggled with a destructive mindset and wasn’t thinking clearly. Critics saw it as one of, if not, the best songs to come from his second album, Man on the Moon II: The Legend of Mr. Rager.
It’s an arena-rocker, full of rock guitars that rage on throughout the five-minute song that’s become a classic slow jam.
Next: Ultimate playlist of sad rap songs
3. Soundtrack 2 My Life
While Jay-Z had “99 problems” and none of them was a woman, Kid Cudi opened his song stating all 99 of his problems were bitches. That’s just one of several references to pop culture and the music industry in the song, with major nods to his mentor Kanye West.
The song would eventually be certified double platinum by the RIAA and made it to number five on the US Bubbling Under Hot 100 chart. Soundtrack 2 My Life was really the synopsis of the Man on the Moon: The End of the Day album, discussing the depression that would eventually consume him and the infinite introspection that would be themes of the album.
4. Man on the Moon (The Anthem)
The title track of Cudi’s debut album and one of the defining songs of his early career, Man on the Moon (The Anthem) helped introduce Cudi’s Moon Man alter-ego. It was released before his debut album on his first official mix tape, A Kid Named Cudi in 2008. It’s an introspection, discussing how Cudi is different, not just in music but in his personal life, so much so, that he’s out of this world. This one song would give three albums life, with all three Man on the Moon albums taking their name from it.
5. Day N Nite
Day N Nite was Kid Cudi’s first real commercial release. Initially found on his MySpace page, it made its way to a few music blogs in 2007 before being featured on his breakout mixtape and a debut studio album.
In the years since its release, the song has been certified quintuple platinum and ranked number seven on Complex’s list of the 100 Best Songs of the Decade for the 2010s. On the Billboard Hot 100, it peaked at number three, eventually even being ranked as one of the best songs of 2009 by Rolling Stone magazine.
Next: Top songs of the 2000s (our full list feature)
6. The Prayer
Kid Cudi’s breakout mixtape gave us a ridiculous number of good songs. The Prayer samples The Funeral by Band of Horses and kind of served as a thank you to the fans that supported him in his early career.
It’s pretty clear that The Prayer is a fan favorite, you’ll see it mentioned on just about every fan blog or fan-voted rankings of Cudi’s songs. Foreshadowing his own death (not for a long time we hope), Cudi considers what he wants his impact to be and envisions how he will be remembered.
Next: Songs about prayer
7. Tequila Shots
Tequila Shots was released at the end of 2020 as part of Kid Cudi’s Man on the Moon III: The Chosen, and in 18 months, would be officially certified platinum by the RIAA.
According to Cudi, it was the first song he made for the album, making it sound like an intro and one that picks up where the last Man on the Moon album left off ten years prior. He wrote it in celebration on the day that his collaboration with Travis Scott, THE SCOTTS reached the top of the Billboard Hot 100, becoming Cudi’s first number-one song of his career.
Next: The top Travis Scott songs playlist feature
8. Erase Me
Kid Cudi’s mentor, Kanye West, stepped in and made a guest appearance on his second studio album to create Erase Me. It served as the lead single for Cudi’s second album, producing yet another Top 40 hit for Cudi on the Billboard Hot 100.
In 2010, Kid Cudi made a guest appearance in the TV show One Tree Hill, starring as himself and performing this song during the episode. Perhaps even better features, both ESPN’s SportsCenter program and the game Guitar Hero Live featured the song for some time.
Next: Top Kanye West songs of all time
9. Just What I Am
Kid Cudi stepped away from the Moon Man persona for his third studio album, Indicud. Just What I Am would serve as that album’s lead single, featuring a guest appearance by King Chip. The song would give Cudi another certified platinum single, with Complex naming the song their 40th best song of 2012. While it only reached number 74 on the Hot 100, it broke into the Top 20 of the Hot R&B/Hip Hop Songs and Hot Rap Songs charts in the US.
10. Cudi Zone
Kid Cudi didn’t miss with his first album, Cudi Zone being the 11th track on the album and a smash hit all on its own. Many fans believe it’s one of his most underappreciated songs, with even Cudi stating it was one of the best raps he’s ever written.
Cudi Zone is all about one thing, the tranquility that comes when you’re completely stoned and at peace with the world. It’s a moment of pure happiness on an album that deals with some pretty deep emotional struggles, a high point of the album both emotionally and lyrically.
11. Frequency
Frequency found its way from Cudi’s SoundCloud to official digital downloads and ended up being one of the first songs from his sixth studio album, Passion, Pain, & Demon Slayin’.
The song kept the stoner, floaty, space vibe of Cudi’s earlier albums that was overall a pretty sick ballad. The video for it was certainly striking, featuring Cudi in the middle of a threesome inside a mushroom cave in the jungle. Critics and fans both loved the song, calling it a return to form for Cudi after he’d done some experimenting after the Man on the Moon I and II.
12. Baptized in Fire
Baptized in Fire is the third collaboration between Travis Scott and Kid Cudi, but it would be far from the last. After the success of Scott’s songs Way Back and Through The Late Night, Baptized in Fire was released with huge expectations. Originally a free release with an album purchase of Passion, Pain, & Demon Slayin’, the song was quickly released onto Google Play and found its way to number three on the US Bubbling Under Hot 100 charts.
13. Show Out
Kid Cudi, Skepta, and Pop Smoke teamed up for this drill rap banger that featured on Kid Cudi’s Man on the Moon III: The Chosen. It’s got a relentless flow and harsh instrumentation that was outside of Cudi’s normal kit, but he throws it down just as well as any drill rapper could have.
Critically, it was named as the worst song on the album by some publications (looking at you Pitchfork and Rolling Stone), but fans loved it. Cudi branching into drill showed the influence of the Travis Scott collabs and saw the song break the Top 12 of the Hot R&B/Hip Hop Songs chart.
14. Mr. Solo Dolo III
Going solo might not always be a bad thing in music, just ask Jason Derulo. For Kid Cudi, his excursion with Mr. Solo Dolo III really delved into his personal struggles with drug addiction and the pain of isolation.
It’s the perfect example of how open and genuine Cudi is when it comes to mental health, showing vulnerability that isn’t often seen in hip hop. In the end, Mr. Solo Dolo III is a perfect Kid Cudi song, diving into the themes he has explored throughout his entire career and fitting right into the Man on the Moon trilogy.
Next: Songs about drugs (a deep dive list)
15. Marijuana
Marijuana is one of the few odes to weed that Cudi has produced, quite fittingly coming in at a length of four minutes and twenty seconds. For Cudi, it’s one of the best songs about cannabis ever. It ended up being another of Cudi’s certified singles, reaching gold status in the US and peaking at number 54 on the Billboard Hot 100.
16. Brothers
Brothers has a bit of a friendlier vibe than other Kid Cudi songs, lacking the depressing isolation that features in many of his songs. Long-time collaborator King Chip and A$AP Rocky appear on the track, two of Cudi’s best friends in the industry.
The song serves as a testament to the relationships and brotherhood you develop with the guys who are always there for you, sending the message that Cudi likes his work best when working with his extended (and not blood) family.
17. By Design
By Design was the first of Kid Cudi’s collaborations with André 3000, one of two songs that made it onto the Passion, Pain, & Demon Slayin’ album. It’s amazing to listen to two great artists rapping about their methodologies in music and views on life. It also highlights how different than most both artists are, which has always set them apart from their contemporaries.
18. Up Up & Away
The final track of Kid Cudi’s debut Man on the Moon album, Up Up & Away segues into the next album with Cudi ready to face new challenges. It isn’t a true end to the album, but really just a transition to the next. It’s also more uplifting than most of the songs on the album, serving as a breath of fresh air to wash away the despair of some of the earlier songs. It’s generally a happy song and the one that Cudi worked on as the very last entry for the album.
Next: The top rap albums of all time (our full list)
19. Dat New “New”
Dat New “New” is one of Cudi’s most debated songs among fans, at least in terms of the song’s meaning. Is it Cudi boasting of fame giving him access to an amazing strain of weed or a boast of his lyrics being fresh and original? Who knows? The song is great, anyway.
20. Reborn
Kids See Ghosts is the hip hop duo of Kanye West and Kid Cudi, the duo that produced this song and included it on their debut eponymous album. It’s all about being reborn from mental illness and coming out the other side as a different person. In 2018, it was one of the best songs of the year according to Business Insider and was the only song from their album to break the Top 40 of the Hot 100, peaking at number 39.
21. Heaven at Nite
Another great song from A Kid Named Cudi mixtape, Heaven at Nite delves into Kid Cudi’s dreams about what heaven must be like.
As a contributing writer for Music Grotto, Dakotah writes and produces professional music/media content. He works closely with editorial staff to meet editorial standards and create
quality content for the Music Grotto website. Dakotah is passionate about music in a wide variety of genres, from hip-hop to country and lo-fi to metal, and he enjoys creating music pieces for Music Grotto.
