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Kid Cudi's 10 Best Features: Critic's Picks

Kid Cudi performs at 2015 Lollapalooza
Michael Hickey/Getty Images

Kid Cudi performs at 2015 Lollapalooza at Grant Park on Aug. 1, 2015 in Chicago.

There’s no other artist like the Moon Man, Mr. Rager himself, Kid Cudi. The Cleveland rapper burst onto the scene with his groundbreaking mixtape A Kid Named Cudi in the summer of 2008, catching the attention of Kanye West, who signed Cudi to his G.O.O.D. Music label.

Breakout single “Day ‘N’ Nite” made Cudi a star as his career quickly took off. Originally a rapper, Kid Cudi showcased several skills in a number of different art forms, including acting, modeling and directing. He released six solo albums and a collaborative project with longtime friend Dot da Genius and influenced a legion of artists who’ve adopted several aspects of Kid Cudi’s artistry into their own art.

There is a facet of Kid Cudi’s career that separates the multi-dimensional artist from his peers: his guest features. Blurring the lines between rapping and singing, Cudi’s catalog of features is just as prolific as his own massive library of songs. His versatility as a singer, rapper and bona fide hook-man has made Cudi a hot commodity in not only hip-hop, but music in general.

After releasing his collaborative album Kids See Ghosts with Kanye West on Friday, Billboard takes a look at 10 of his best guest features in hip-hop. The list below highlights choruses sung by Cudi as well as rap verses, in case any of you forgot Cudi’s skills on the mic.

10. Consequence & Kid Cudi - “Buggin’ Out 09”  

In 2009, Kid Cudi teamed up with Queens rapper Consequence to remake the A Tribe Called Quest classic “Buggin’ Out.” The record features Consequence and Cudi mimicking Phife Dawg and Q-Tip’s first verses, respectively. Consequence delivers a solid verse, but Cudi steals the show with a closing verse rapping about the massive buzz he’s been getting while never compromising his Martian lifestyle.

The song arrived after Cudi’s critically acclaimed mixtape A Kid Named Cudi, and at that point in time, Cudi’s popularity was booming. Magazine covers, crossover features and a number of recordings kept Cudi busy. But, as his verse explains, while we want more of Cudi, we can’t forget to go get our own.

9. King Chip feat. Kid Cudi - “Ask About Me”  

Early in his career, Kid Cudi released a selection of classic collaborations with his hometown brethren King Chip. Their 2009 effort “Ask About Me” is by far their most popular song together. Cudi opens the song with an excellent verse rapping about a number of things, including his fashion sense, musical ability and popularity. Chip follows with an equally superb verse, going at Cudi with the bars. These days, Cudi is recognized more for his singing and melodies, but he can also hold his own on the mic and ride a beat with his multi-level flow.

8. Kanye West feat. Kid Cudi & 070 Shake - “Ghost Town”

The song from Kanye’s most recent effort Ye features Kid Cudi portraying an internal persona of Kanye's that’s pleading to be loved and adored. G.O.O.D. Music’s newest signee, 070 Shake, also portrays a persona of Kanye that feels like a kid again with no sense of pain. In the context of the mental-health aspect of Ye, Cudi’s brooding vocals over the rock-inspired beat displays the feeling of trying to love yourself more but losing a sense of who you are in the process. Cudi’s precision seamlessly segued over to him and Ye’s joint effort, Kids See Ghosts.

7. Jackie Chain feat. Kid Cudi - “Rollin”

The 2009 collab between Kid Cudi and Alabama rapper Jackie Chain is another example of Kid Cudi’s superb lyrical skills he displayed earlier on in his career. The hazy, lean-inspired song is a look into the drug and alcohol-fueled nightlife of Cudi and Jackie Chain. Both artists discuss their eventful night of reaching higher levels of intoxication all the while trying not to lose their minds. Cudi’s syrupy slow flow has the Cleveland rapper feeling right at home on the Southern-influenced beat, complementing Jackie’s drawl.

6. Travis Scott feat. Kid Cudi - “through the late night”  

Since the beginning of his career, Travis Scott has mentioned the massive influence Kid Cudi had on his music. Before the release of his second studio album, Birds in the Trap Sing McKnight, one of Travis’ biggest goals was to work with Kid Cudi, and he got his wish with “through the late night.” The song opens with Cudi’s iconic melodic humming that leads to an opening verse about the night-crawler lifestyle.

This lifestyle, which includes partying, drugs and sleeping during the day, is nothing new for these ragers. Cudi plays on the “Man on the Moon” aesthetic that’s driven his entire career, and he’s welcoming the vibe, along with the psychedelic drugs that induce the spacey, galactic feeling that Cudi is rapping about.

5. Kanye West feat. Kid Cudi - “Welcome to Heartbreak”

“Welcome to Heartbreak” is the first song in the decade-long catalog of Kanye West and Kid Cudi collaborations. It’s the only feature Cudi had on Kanye’s fourth studio album 808s & Heartbreak, but it also signified the massive influence he had on the entire album. Kanye and Cudi give their listeners an emotional song that talks about the sadness and anger Kanye has toward the “good life.” This perceived “good life” keeps Kanye away from his family and friends who are getting married and starting families -- a life Kanye really wants but knows he can’t have.

As Kanye takes us into the depths of his anguish and despair, Cudi’s minimal chorus is the rope that pulls us back to the surface, singing, “And my head keeps spinning/ Can’t stop having these visions/ I gotta get with it.” It’s a quick moment of hope and determination that we instantly miss when Kanye flirts with hopelessness on each of his three verses.

4. Kanye West feat. Kid Cudi - “Guilt Trip”

Kid Cudi’s interlude on “Guilt Trip” from Kanye’s sixth studio album,Yeezus, wasn’t favored by the man himself. This verse was recorded during the making of Watch the Throne, but it made the cut for Yeezus. Cudi explained he would have rather re-recorded the vocals and felt underused. Despite the revelation, this is one of Kanye and Cudi’s most memorable songs. Cudi creeps onto the song with an emotional, melodious voice asking why his loved one left him.

As he sings each note, you can feel the pain in his proclamation, as his voice travels along the intergalactic beat. Despite the lukewarm response from Cudi, this song shows Kanye’s ear for elevating his records with a great Kid Cudi feature.

3. Kanye West feat. Kid Cudi & Raekwon - “Gorgeous”

“Gorgeous” is a look into social injustices in America as well as disillusionment and sexual exploitation. In an interview with MTV News in October 2010, Kid Cudi explained how bad he wanted to be on “Gorgeous” from Kanye’s fifth studio album, My Beautiful Dark Twisted Fantasy. “‘Gorgeous’ was one of those records that, as soon as I heard the beat, I was like, ‘Man, this is the one.’” Cudi had to lie about having an idea for the track just to get on it, and thankfully Kanye took the idea.

Cudi found his way onto the song, providing a harmonious voice that fits perfectly between Kanye’s anger and Raekwon’s wisdom. As Kanye gives his views on social injustices and Raekwon offers solutions to said injustices, Cudi’s hook arrives over a melodic chord of an electric guitar, singing about the desires of fame and not letting up on that chase of fame.

2. Kanye West feat. Kid Cudi - “Father Stretch My Hands, Pt. 1”

“Father Stretch My Hands, Pt. 1” once again shows the musical brilliance that comes out of a Kanye West and Kid Cudi collab. If the Pastor T. L. Barrett sample and Future’s Metro Boomin drop aren’t enough to carry this song, Kid Cudi singing “Beautiful mornin’, you’re the sun in my mornin’, babe” takes it to astronomical levels. Cudi’s compliments to that special person in his life is a warm and bright chorus that causes fans to lose their minds whenever it’s on. With this being their fourth entry on this list, Kid Cudi and Kanye West have a very special chemistry when it comes to making a song.

1. Kanye West feat. Kid Cudi, Pusha T, Lloyd Banks, John Legend & Ryan Leslie - “Christian Dior Denim Flow”

G.O.O.D. Fridays was a period of 15 weeks in late 2010 where Kanye West released a track every week featuring members of G.O.O.D. Music and other frequent collaborators. “Christian Dior Denim Flow” was one of the best records to come out of that batch of songs. The story behind this song is that Cudi wanted his verse removed shortly after recording it, feeling that his effort didn’t fit with the rest of the record. Kanye instead kept Cudi’s verse, and the result was an amazing display of lyricism and cohesion, reminiscent of the days where posse cuts reigned supreme.

Cudi already delivers a spirited chorus alongside John Legend, but it’s his closing verse that steals the show. In it, Cudi flows on the beat rapping about living a better life -- taking his mother to Chanel, no longer needing counseling -- while telling us we only know half his story and not really knowing what’s affecting him mentally.

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