On May 14 Live Nation announced a comedy treat as GRAMMY winners Dave Chappelle and Jon Stewart will reunite for the first time since their August 2017 performances at Radio City Music Hall. They'll be performing in Boston on June 11–13, Houston on June 21–22 and El Paso, Texas, on June 23–24.

In addition to being long-time friends, Stewart and Chappelle each have the unique distinction of having won each time they received a GRAMMY nomination.

The 60th GRAMMY Awards brought Chappelle his first GRAMMY nomination and win for Best Comedy album, as The Age Of Spin & Deep In The Heart Of Texas offered the comedian's top-rated Netflix specials on audio. He also made a cameo appearance on stage with Kendrick Lamar and U2, in an interlude before "DNA," after their performance of "XXX" on the telecast, saying, "I just want to remind the audience that the only thing more frightening than watching a black man be honest in America is being an honest black man in America."

Stewart, who is bringing his comedy back to cable on HBO, is remembered for hosting "The Daily Show" as well as hosting the GRAMMY Awards in 2001–2002. At the 47th GRAMMY Awards Stewart's The Daily Show With Jon Stewart Presents…America: A Citizens Guide To Democracy Inaction won Best Comedy Album. At the 53rd GRAMMY Awards his The Daily Show With Jon Stewart Presents Earth (The Audiobook) won Best Spoken Word Album.

Registration for Ticketmaster's Verified Fan Platform is now open and tickets for the June dates will go on sale to registered fans on May 18.

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