Although he has pondered retirement and has basically declared his next album his last, Kid Cudi already has enough high-quality music in his catalog to be considered a hip-hop legend. Albums like the Man on the Moon trilogy and his Kanye West collaboration Kids See Ghosts have demonstrated a unique singing and songwriting ability that has never been replicated in the genre.
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In the midst of crafting what he dubbed “album of the year” earlier this month, we felt it necessary to remind fans why new music of his is always in demand. With each LP, he finds ways to put a new spin on his timeless sound.
Here are his 10 best songs.
1. “Down & Out”
In 2008, the Cleveland-bred budding star released his debut mixtape A Kid Named Cudi. Introducing himself to the world with the tape’s intro “Down & Out,” the then-24-year-old gave fans a glimpse of his raunchy, yet melodic style and his particular hip-hop influences. Using the same beat from “Chonkyfire,” produced and performed by Outkast on their third studio album Aquemini, “Down & Out” is the No. 1 essential go-to song for any Kid Cudi fan.
2. “Soundtrack 2 My Life”
The second song on his 2009 debut album, Man on the Moon: The End of Day, “Soundtrack 2 My Life” couldn’t be more to the point. As he consistently documented throughout his career and primarily focused on with his first couple of albums, Cudi delves into the harsh specifics of his not-so-ideal mental health. Rapping about being close to resorting to drugs and suicide, the upbeat sonics accompanied by depressing portrayals epitomize Cudi’s artistry.
3. “Reborn”
One of the happier and more blissful songs of Cudi’s entire career, “Reborn” sees the patented humming he perfected over the years on full display. The I’m so—I’m so reborn, I’m movin’ forward hook can create a weeks-long earworm for listeners, as it sandwiches potent verses from Kanye West at the peak of their now-defunct friendship.
4. “Day ‘n’ Nite”
Without question, “Day ‘n’ Night” is the most popular song Cudi has ever released as a solo artist. Debuting at No. 3 on the Billboard Hot 100, the song captured the attention of the entire nation in 2009 and awakened a youth looking for a musical idol. As the lead single for Man on the Moon: The End of Day, Cudi could not have used a better track to officially introduce himself to the mainstream world.
5. “Mr. Rager”
The first time he explicitly mentions his alter-ego Mr. Rager, Kid Cudi uses this song and the album it lands on, Man on the Moon II: The Legend of Mr. Rager (2010), to go even further into the darkness. Exploring depression and suicidal thoughts on MOTM1, the sequel sees songs like “Mr. Rager” display true anguish, and make it easier for listeners to empathize and relate to Cudi.
6. “By Design”
As previously mentioned, Outkast was surely one of Cudi’s biggest inspirations when he first got into music. Seven years removed from his tribute to them on “Down & Out,” Cudi was able to connect with Andre 3000, one-half of the legendary duo, for “By Design.” As his most psychedelic and ethereal sounding project in his discography, Passion, Pain & Demon Slayin‘s best song, “By Design,” encapsulates the LP beautifully.
7. “Dat New New”
Many of Cudi’s best songs, like “Down & Out” mentioned above, came during the period before he began crafting studio albums. “Dat New New,” released as a single in 2008, sees the more confident and brash rapper inside of Cudi that he only unleashes occasionally. Being one of the first displays of this beloved swagger, “Dat New New” is an early highlight from young Cudder.
8. “Enter Galactic”
Romance was always viewed as a gift and a curse to Cudi. Songs relating to love in his catalog either referred to the euphoria of being lovestruck or the pain involved with heartbreak. On “Enter Galactic,” he depicts the thrilling combination of love and drugs better than he ever did before or after this song’s release. “Enter Galactic” is the ninth song on Man on the Moon: The End of Day.
9. “The Prayer”
Another gem from his pre-studio album days, “The Prayer” is track six on his 2008 A Kid Named Cudi mixtape, re-released and updated in July 2022. Interpolating the classic bedtime prayer with the If I die before I wake / I pray the Lord, my soul, to take hook, “The Prayer” sees Cudi at his most somber and reflective.
10. “Tequila Shots”
Reintroducing himself to hip-hop after a four-year hiatus from solo music, Cudi’s trilogy ending Man on the Moon III: The Chosen (2020) showed a reinvigorated and energized Cudi. The best example of this was the LP’s second song “Tequila Shots,” which he hoped would be the first song to revive fans’ love for the MOTM trilogy that he hadn’t revisited in a decade.
“It sounds like such an introduction, it sounds like you pick right back up where we left off ten years ago,” he said in an interview with Apple Music’s Zane Lowe.
Photo by Rebecca Sapp/Getty Images for The Recording Academy
