Actor Cheyenne Jackson kickstarting musical ambitions 

click to enlarge Cheyenne Jackson
  • Photo by Karl Simone
  • Cheyenne Jackson is bringing his show to Feinstein's at the Nikko.
For the first time, Broadway and TV heartthrob Cheyenne Jackson will take the stage at Feinstein’s at the Nikko, 222 Mason St. The openly gay actor is best known for his comedic arcs on “Glee” and “30 Rock,” but his career first flourished onstage with roles in Broadway’s “All Shook Up” and “Xanadu.”

Jackson will perform at the 140-seat cabaret-style venue Friday and Saturday. The sold-out shows will consist of classics from his one-man show, “Music from the Mad Men Era,” as well as contemporary tracks off his new album, “I’m Blue, Skies,” which includes three songs he co-wrote with singer-songwriter Sia Furler.

“I met Sia three years ago at the OUT 100 photo shoot, and it was love at first sight,” Jackson told The San Francisco Examiner. “She is one of the most musically sophisticated and innovative artists I have ever worked with.”

In addition to launching his music career, Jackson said he is kicking off the new year by exploring riskier roles on television. He has signed on to be in Ryan Murphy’s HBO pilot about open relationships. Jackson, himself in sober recovery, will play a meth addict.

“It will be quite the water-cooler-moment type of show,” Jackson said. “Blunt, witty and sexually intriguing.”

Along with Matt Bomer and Zachary Quinto, Jackson is one of the few leading men trumping the notion that gay actors can’t be taken seriously in straight roles. What’s interesting to note here, however, is that these actors are all extremely good looking, even by Hollywood standards. And with that comes an intense fascination with whom these fine gay men are sleeping with.

In September, Jackson filed for divorce. A month later, he publicly began dating a fellow actor. At the same time, Jackson shaved his head, grew a mustache and got Elvis Presley lyrics tattooed on his arm. The media labeled the drastic transition for the once clean-cut actor as a sign of a midlife crisis. “I have had quite a difficult and transitional year, so I want the audience to be privy to that and share my story with them,” Jackson said.

At least physically, Jackson has already shared quite a bit. Teasing the new HBO show, the actor, who has already appeared nude onstage, admits he has no caveats when it comes to getting naked for a role if it’s “germane to the story.”

Of course, savvy gay readers and even mildly proficient smut researchers will have already gotten up close and personal with Jackson’s private parts. Earlier this year, a sex tape surfaced allegedly depicting Jackson masturbating. Jackson has played coy and neither confirmed nor denied the authenticity of the clip.

Despite this newfound reputation as a 38-year-old bad boy, Jackson said settling down and raising a family is something he’s always wanted.

“I have known I was going to be a dad as long as I can remember,” he said.

Perhaps proof that he is going in that direction, Jackson tagged his most recent Instagram selfie with his boyfriend #WeAreWellAwareHowAnnoyingWeAre.

Oscar Raymundo is the author of “Confessions of a Boy Toy.” Email him at

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Oscar Raymundo

Oscar Raymundo

Oscar Raymundo is the author of Confessions of a Boy Toy. Email him at
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