Dave Chappelle hosted a star-studded surprise comedy show at the Peppermint Club in Los Angeles on Wednesday night (Sept. 19). Joining the comic for a turn on stage was the multi-hyphenate Will Smith (making his stand-up debut, with wife Jada Pinkett Smith and daughter Willow in attendance), basketball giant and recent L.A. transplant LeBron James, Jon Stewart, Michelle Wolf, Katt Williams, Michael Che and John Mayer, who provided background guitar work and the occasional zinger.
Few of those gathered at the private venue expected such high-wattage guests, though a mandatory lock-out of all mobile devices should have offered the first clue. Indeed, there was not a cell phone in sight as jokes delivered tackled such topics as the #MeToo movement, race and religion. “Comedy ‘Fight Club'” was how Chappelle described the night, which offered more than three-and-a-half hours of belly laughs. The show also had its serious moments. Jon Stewart made an impassioned plea for gun control; Williams sang a hopeful tune for LeBron James’ arrival to the Lakers (for his part, James didn’t say much); and Wolf took on women’s issues and the gender divide.
As for Smith? He explained to the crowd that his 50th birthday was coming up and doing stand-up was on his “bucket list” and that he was filming the experience for a show called “The Bucket List” (next week, he bungie jumps from a helicopter over the Grand Canyon). His repertoire revolved mostly around life at home with the family. “I kind of lost control of my house,” joked Smith, noting that his wife’s “Red Table Talk” show on Facebook Watch has turned the garage into a control booth (a bewildered Smith made light of how his ex-wife Sheree got booked for the first episode). Meanwhile, son Jaden had a song that was taking off (“Icon”) but wouldn’t let his dad be featured on the track. Cracked an incredulous Smith: “He looked at me like I was the second-best rapper in the house!”
Smith also joked about joining social media and broke stride mid-way through his performance to acknowledge his family sitting feet away. He later did rap a bit for the night’s grand finale, when all the participants gathered on stage and Chappelle declared, “There’s a new sheriff in town!”
Also honing his comedy chops was John Mayer, who mused on pornography (“Why are all porn videos rated 73%?”) and his own sex life, but mostly served as a musical guide — Mayer jammed through songs from “Footloose” and “Caddyshack” and tunes by Nirvana, Pearl Jam, Prince and Jeff Buckley with equal aplomb — and Chappelle foil.
Chappelle made one mention of Louis CK, whom he referenced in his most recent Netflix special, asking the audience how they would react if the shunned comedian showed up and started masturbating openly. When the question was met with mostly silence, he cracked, “[some] brave women” here. Chappelle also jabbed at the sexual exploits of Jamie Foxx, Aziz Ansari and Mayer, name-checking Taylor Swift.
Other highlights included Chappelle’s mockery of the book “The Secret” and, more heartfelt, his comparison of Kanye West to Jack Johnson, the first black heavyweight champ in the world.
Surprisingly, Stewart, who retired from his nightly talk show three years ago, steered clear of politics for the most part (in one mention of Trump, he compared his presidency to the end run of a Broadway show, where you started with Nathan Lane and ended up with “Sanjaya from ‘American Idol'”) and instead joked about his appearance explaining that “Jews age like avocados” and offering, “I want you to know that I know I look like this.” The rest of Stewart’s set revolved around stories of the cultural divide in his house, between his own Jewish upbringing and his wife’s Catholicism.
Che’s was the shortest set and consisted mostly of the “SNL” star and Emmys cohost making the case for New York City as the ultimate “drinking town,” and certainly over L.A. though Chappelle and his all-star crew seemed hell-bent on proving otherwise.
The night, which also featured performances by Donnell Rawlings, Ashley Barnhill and Mohammed Amer, was organized by John Terzian, cofounder of The h.wood Group, who, along with Brian Toll, owns The Peppermint Club.