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In some productions of “Hamlet,” the moments when incestuous Gertrude counsels her melancholy son are solemn — downright uncomfortable, even. But in “Hamlet! The Musical,” featuring Alexandra Billings, the Chicago diva born Scott Alexander Billings, Gertrude’s advances are cause for elaborate celebration.

“That’s my song — `Mama Is a Boy’s Best Friend,'” says Billings, who plays Gertrude in the musical, which opens Thursday at the Chicago Shakespeare Theater on Navy Pier. “It’s a great number — a bunch of grinds and hip thrusts! And a boa! It’s red! Who could ask for anything more?”

Leonardo DiCaprio couldn’t have jazzed up the bard any better. And while Shakespeare’s company was known to hire the occasional cross-dressing actor, even he might have blinked at this particular Gertrude, an imposing figure who began her career as a female impersonator at The Baton, Chicago’s premier drag-queen show lounge.

An update of Billings’ popular collaboration with scriptwriters Jeff Richmond and Michael Thomas, “Hamlet! The Musical” first ran about four years ago at the ImprovOlympic. “I think it’s funnier, if that’s possible,” says Billings, by phone from her Chicago home. “Without giving too much away, I think it’s a little bit more absurd and a little bit more outrageous [now]. Which is always a good thing.”

A Los Angeles native who moved to Schaumburg as a teenager, Billings began her acting career at the Baton as Shante, and eventually won drag contests all over the U.S. Then Billings underwent transsexual surgery, and began landing roles in late-night stage productions such as “Shannen Doherty Shoots a Porno” and “Vampire Lesbians of Sodom” and “Cannibal Cheerleaders On Crack.” Today, she’s a prolific actress and cabaret singer, having portrayed Cruella DeVille in a stage version of “101 Dalmations,” acted with champion Olympic swimmer Greg Louganis in activist Larry Kramer’s “Just Say No” and acted in various Steppenwolf Theatre productions. She also has a new CD, “Being Alive.”

But playing Gertrude at the prestigious theater is a stretch. “The whole thing is terrifying,” Billings says. “I’m really nervous about this. The only consolation I have is I know the show is really funny and it’s really well done. Seriously, all I have to do is go wear my costume on stage and it’ll be fine.”

“Hamlet! The Musical” is neither a faithful “Hamlet” adaptation nor a complete parody, although song titles such as “Something Stinks” (as opposed to something being rotten in the state of Denmark), “What’s the Matter With Hamlet?” and “The Drinking Song” suggest its main thrust is not scholarly erudition. And it’s not really improvisational, even though it began life at ImprovOlympic and is being co-presented on Navy Pier by Second City, “because there is a script and the script stands by itself,” Billings says. “But I think in this script Jeff and Michael have left room for occasional thises and thats.”

“Hamlet! The Musical” is the right mixture for Billings, who alternates between over-the-top comedy and straightforward drama roles. (Shakespeare’s Gertrude isn’t the only Gertrude she has portrayed; one of Billings’ most notable early roles was in the dramatic “Gertrude Stein and a Companion.”)

After a few “Cannibal Cheerleaders”-style productions early in her career, Billings wanted to avoid campy roles. “It’s kind of like being in the same job for five or six years,” she says. “You just begin to feel, `This is a great job, but I really want to do something else for a little while.’ I know this is going to sound a little philosophical, but I think when you put things out in the universe they come back to you. I put this out there and it came back. And I got really lucky.”

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“Hamlet the Musical” opens at 8 p.m. Thursday at the Chicago Shakespeare Theater, Navy Pier, 600 E. Grand Ave. It continues at 8 p.m. Thursdays, 8:30 and 10:30 p.m. Fridays and Saturdays and 3 p.m. Sundays through Aug. 20. Tickets are $20. 312-595-5600.