Iconic Drag Artist Karen Valentine Added To ART COLLECTORS CHOICE AWARDS Jury

Thom Bierdz
6 min readJan 10, 2024

One of Milwaukee’s most beloved entertainers, Karen Valentine (K.V.), has been added to the impressive list of international art collectors deciding the winning artists in the upcoming Art Collectors Choice Awards.

After 15 years of success introducing phenomenal contemporary artists around the globe to USA’s best galleries, American Art Awards launched the similar World Art Awards (in 2023). Both those prestigious international art competitions award top galleries and museums — who later vote on 50 categories of online art images from 70+ countries — awarding hundreds of amazing artworks annually.

Launching now in 2024, the similar Art Collectors Choice Awards will not be scored by galleries — but instead by an assortment of 20 revered art collectors, like Karen Valentine.

K.V. studied at the Milwaukee Institute of Art & Design (MIAD), took art courses/classes at the Chicago Art Institute and also the Milwaukee Art Museum. Through a four-decade career of performing and writing, she has covered, promoted, and lobbied the importance of the arts at almost every venue imaginable.

“The arts are in me — my soul, my blood stream, they speak to me. When I wonder upon a person who can communicate to me on that special level, it’s the Ultimate Gift! My foundation, the Valentine Fund for The Arts, Culture, and The Humanities, provides gifts and awards to outstanding arts programs, art therapy programs, performing and applied arts that excel or have the potential of excelling.”

Milwaukee crowds have been awed by the entertainer since the 1980’s. K.V. is the consummate emcee, cabaret singer, comedienne, socialite and designer. Magazines tout her as a brilliant combination of glamour, wit, sophistication and charm — who lives life with tongue firmly planted in cheek!

“The best party I have ever been invited to…,” she pauses, “ …is life!” — which is why she shines exuberantly at cocktail parties, art openings, fashion shows, book signings, derbies, theatre openings, auctions, and fundraisers.

People adore her talents, humor and authenticity — and she adores theirs’. She also adores all forms of art — applied/performing — and all tastes, “good and bad alike!,” she smiles, then cringes.

Ensconced ever so comfortably in the deliciously delirious DairyLand of the Midwest, K.V. is not one to sit home making cheese curds. She’s someone special at some place special every week. And every midmonth (Saturday closest to the 15th) she headlines a cocktail hour show at 5PM at La Cage “Bosom Buddies,” a send-up salute to the Great White Way, with gal pal, Maple Veneer.

Club Charlies in the heart of The Historic Third Ward has K.V. monthly hostessing “SunDay Fun Day Show Tunes” along with V.J., Bradley Fell. K.V. leads sing-a-longs, toe-tapping, head bopping to Broadway, television, movies, and other clips of songs and production numbers. With the dramatic Karen Valentine in charge, audiences eagerly participate — and “shenanigans are always unpredictable hijinks' — and everybody is the star!”

The new year (2024) has presented a present, a new gig for K.V. — hosting BINGO, which she has mastered previously at both Fluid and Hamburger Mary’s. K.V. returns to handling the balls once again and this time at Miss Katie’s Diner, a popular eatery located near the revered Marquette University (which has hosted many a president and first lady when visiting the Cream City).

Her private time at home is not altogether private as she still engages the masses by penning her well-read column of 25 years, “Cordially Yours” (now published online via Milwaukee Pride Lives — MPL.)

Her innumerable internet followers never miss, “So A Drag Queen And A Leather Man Go Into A Bar,” a podcast she co-hosts with friend Ursus. The monthly free-form hour long chat hits hot topics, “leaving nothing sacred. It’s fascinating how similar and yet alike two opposites like us can be…” she muses.

Got a yearning for old time cabaret? Exclusive to The Milwaukee Market, K.V. sings with pianist Dr. Gino DeLuca, maintaining two new productions annually. The last celebration at the Skylight Music Theatre was sold out two weeks before the performance.

The broad, or dame, or belle of the ball has also entertained while bar tending off and on for nearly two decades at Switch, the Room of Boom, Red Star, upstairs of the Trocadero, and This Is It (Wisconsin’s oldest LGBTQ+ Bar dating back to 1968, thriving under current co-owner Trixie Mattel).

In 1985, the extroverted K.V. was one of the founders of the Gay Choral Movement, which developed into the Fest City Singers, from there an offshoot the Cream City Chorus. (To this very day, a Gay Chorus is still very active in the Milwaukee community making a joyous sound.)

K.V.’s greatest legacy to date is her Valentine Fund; a fund for the arts, culture, and the humanities — financially assisting LGBTQ + organizations with applied/performing arts departments.

When asked how it feels to be a light in the dark, K.V. wipes a tear, “Assisting in or setting up art therapy programs makes such a difference to these youngsters. They’ve put down guns and knives and fists and in their trembling hands I stuck paint brushes, cameras and modeling clay!”

Milwaukee’s legendary K.V. graces two epic books on drag: Harry James Hanson and Devin Antheus’ “Legends of Drag: Queens of a Certain Age” (06/21/2022) and “A History of Milwaukee Drag: Seven Generations of Glamour” by Michail Takach and B.J. Daniels 2022.

K.V. sums up her careers, “As earlier stated, life is the best party I’ve ever been invited to ! Let’s make it art!”



Thom Bierdz

One of Medium’s TOP ART CONTRIBUTORS, award-winning author, actor, film-maker, painter. 12 books: 6 on art. President of WAA & AAA & ACCA.