She and her shadow (All images by Matthew Rettenmund)

Jimmy James is a live performer who blew my young mind on January 18, 1991.

By that time, I — at 22 — had spent a good dozen years obsessing over Marilyn Monroe, who was in vogue again throughout the '80s. I read all the bios and visited those mall stores filled with airbrushed Marilyn posters that were the perfect combo of retro and of-the-moment. I rented her movies, bought an incredible vinyl album with (and memorized) all of her songs and best movie one-liners. Boomers were so powerful they made Gen X respect the favorites of their youth in a way Gen X will never, ever get Gen Z to do — numbers-wise, we simply don't have the range.

My drawing on a folder of Jimmy circa 1991

So when I saw that a person named Jimmy James, a female impersonator, as we called them then, was coming to one of my fave clubs in Chicago, the aptly named Vortex, where innocence went to die, I made sure I was there. I watched Jimmy from the second floor, gape-jawed at the completeness of the illusion he created, looking every inch the glamour queen. To say he captured Marilyn in spirit is to mean he brought her back from the dead. He had her zaftig form, her gown (the original of which was recently defiled by Kim Kardashian), her cotton-candy hair and her speaking and singing voices. The spotlight was like a halo as we peeked into Marilyn in heaven.

Presuming I have my dates right, Jimmy was already well into what would become a 35-years-and-counting-long career, having KILLED on Donahue in 1987. I was so happy I got to see him, and I was also happy this weekend to discover the San Antonio resident was putting on a show not only in my current hometown, NYC, but three blocks from my apartment! Sub-zero temperatures? Who cares? I could have walked over there naked and avoided any Prince Harry frostbite.

Every performer's dream front row! They were his friends, but it became a running gag.

As Jimmy joked during his informal, infinitely warm set, the location was basically Port Authority. “My career is over if you ever see me with a doll,” he quipped as he hauled out Kermit the Frog for a duet, ç (In reality, the space, run by Daniel Nardicio, is perfect for a show like this.)

The rainbow-flag connection

I find it so interesting that Jimmy's former vocation — he no longer gets into Marilyn gear — was so dependent on building up an image while his stage show is much more about self-deprecation and relatability. He puts on no airs at all, telling us that in hopes of making it back to NYC post-pandemic, he bargained with a portrait of St. Jude that hangs in the home he shares with his 88-year-old staunchly Catholic mom every time he passed it to pee.

Blowing kisses to A-list guest Ruby Rims

Referring to his shirt as a tent, all of us who have packed on some pounds since 2020 could share a snort.

But as charming as he is, he also strives to deliver, and while we receive precious little Marilyn (he does conjure her briefly in an encore), there are plenty of other divas the One and Many Jimmy James still channels, including Billie Holiday, Eartha Kitt, Cher, Judy Garland, Liza Minnelli and Barbra Streisand. His Bette Davis is a hoot, and the increasing huskiness of his instrument allows him to bring her forth in full effect. 

The exciting part of Jimmy James live is he is equally adept at humor and even camp (his Cher medley will have you asking WTF MDNA is) and at vocalizing. He sings his own viral hit “Fashionista,” too, and cares about how he sounds — unlike many drag legends, he isn't lip-synching for his or anyone else's life.

Jimmy put asses in the seats, but this was the ass I was curious about.

I think Jimmy might have a great dramatic performance in him, too. For example, I was a little misty when he segued from guffaws to a nostalgic video package showcasing his Marilyn years set to Lana Del Rey's “Young and Beautiful.”

“Will you still love me when I'm no longer young and beautiful?” It's a question most great stars think — but never ask aloud. It had me remembering the fact that I'd last seen him perform over 30 years ago, an impossible expanse of time.

Considering the enthusiastic response Jimmy received this evening, I would say the answer is: We'll let you know when that happens, babe.