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Kid Cudi jumped onstage with Kanye in Chicago, and now he's defending every second of it

Ye's Soldier Field homecoming was already a spectacle. Then Cudi walked out - and the internet had a lot more than music to argue about.

Kid Cudi jumped onstage with Kanye in Chicago, and now he's defending every second of it

Two nights at Soldier Field. A reunion nobody quite expected. And then, the morning after, a prolonged argument on X that pulled in half of hip-hop Twitter. Kanye West's Chicago homecoming concerts on September 3 and 4 were already being called some of the most star-studded shows of the year - and then Kid Cudi walked out, and the story got a lot more complicated.

West had been through considerable controversy in the years leading up to the shows, but fans in his home city put all that to the side on Friday, September 4, to see the final of his two homecoming nights at Soldier Field - his first Chicago performance in five years. The guest list alone was staggering. Kanye packed the second night with hometown heroes Chief Keef, Twista, and Lupe Fiasco, and also brought out Rick Ross, Don Toliver, Travis Scott, Young Thug, and CyHi.

But the guest that broke the internet wasn't any of them.

Cudi made a surprise appearance during West's second Chicago concert at Soldier Field on September 4, and the two artists performed together, bringing back memories of their long history as collaborators. According to Complex, Ye staged a G.O.O.D. Music reunion with Big Sean, 2 Chainz, Common, and surprise guest Kid Cudi, who joined him for "Father Stretch My Hands Pt. 1" and "Ghost Town" before performing "Pursuit of Happiness." Setlist.fm logged it as the first public collaboration between Ye and Kid Cudi since August 2024.

The backstory is what gave the moment its weight. The public fallout between the two began in February 2022 when Kanye removed Kid Cudi's contributions from Donda 2. Kanye was upset over Cudi's close friendship with Pete Davidson, who was dating Kanye's ex-wife Kim Kardashian at the time - and Kanye declared on social media that Cudi would not appear on the album, leading Cudi to fire back that they were no longer friends. And then, as Deadline reports, following West's antisemitic behavior, including a pro-Hitler song, for which he apologized with a full-page ad in The Wall Street Journal in January, Cudi told West he was "done" with him.

So when Cudi walked out onto that stage Thursday night, a lot of people had opinions.

New York radio personality Peter Rosenberg was the first major voice to go public with criticism. Rosenberg wrote on X that he was "disappointed in a lot of people," posting on September 4 and saying the reunions had come only a year after West had made deeply offensive remarks. Cudi's response was direct and personal. Deadline reports that Cudi told Rosenberg he didn't "really care if ur disappointed in me" and wrote, "That man is my brother. U don't have a relationship w him like I do. Damn near 2 decades of art and friendship."

He didn't stop there. Cudi added that West "was dealing w mental health struggles for years and now he's good" and that "everyone deserves some grace when they family." According to WION, Cudi revealed he eventually forgave West because West gave him a sincere, personal apology - something Cudi noted West rarely does for anyone.

The first night, September 3, was no slouch either. Big Sean made a surprise appearance, pulling from the G.O.O.D. Music compilation Cruel Summer and his own Dark Sky Paradise across a setlist totaling over 40 songs from Ye's catalog, with Twista, 2 Chainz, and Future also joining Ye atop his traveling globe-like stage. HotNewHipHop also noted that Kanye took a moment to salute Lil Durk, who is currently on trial facing murder-for-hire charges, by playing Durk's J. Cole collab "All My Life." That detail, too, drew its share of online commentary.

The Cudi situation cut deeper than a typical celebrity friendship story, though, because of the specific history involved. Cudi addressed the backlash in a Saturday social media post following Rosenberg's comments condemning people who have remained close to West despite his past antisemitic remarks. Cudi's posts stayed up. He didn't walk anything back.

What Rosenberg said in return was pointed: that he wasn't necessarily calling out Cudi specifically, but that seeing people rush back into Ye's orbit a year after a "Heil Hitler" song was the thing that stung. The two went back and forth publicly for most of Saturday, with neither side blinking.

The wider guest list at both shows - which also included Lupe Fiasco, Travis Scott, Big Sean, Common, Young Thug, Rick Ross, Don Toliver, 2 Chainz, and Chief Keef on the Friday night alone - will keep people talking about whether Ye's rehabilitation in hip-hop circles is moving too fast, too slowly, or whether that's even the right frame. Cudi's answer, for now, is simple: the friendship predates the controversy, the apology was real, and the stage was where they belonged.

The setlist from night two still had a few songs listed that never got played - "Faneto," "Through The Wire," "Say You Will" among them. Those songs were on the paper setlist but were ultimately not performed. Maybe next time.

Sources