March 17, 2026 | Jamie Taylor

Dear Ruthie: charming the crowds with heart, humor and high hair

From writing an advice column to becoming a global media sensation, Milwaukee’s own Dear Ruthie is a true trailblazer.

Dear Ruthie

"Comparison is a thief—so lock your friggin' doors."

Dear Ruthie began her drag career in the late 1990s, writing the advice column "Dear Ruthie" for the Wisconsin Light. She began appearing in Milwaukee drag shows and quickly became known as the "funny girl." Over time, her advice column would be published in several LGBTQ publications, including Quest, InStep and OutBound.

Ruthie eventually landed a spot as a roving reporter on "The Don & Bo Show," a TV series on CBS58. She was the first drag performer to be a weekly regular on any TV show in Milwaukee. This primed Ruthie for a larger TV role, as Camp Counselor Ruthie on the reality drag show "Camp Wannakiki," which aired for six seasons on OutTV. The streaming show, which aired throughout North America and the United Kingdom, became a cult favorite.

In 2013, Ruthie launched her charity, Ruthie's Kennel Club, raising money for local animal-related charities throughout Wisconsin. Similarily, Ruthie raised hundreds of thousands of dollars for local charities by hosting weekly drag bingo events in downtown Milwaukee.

During her career, Ruthie appeared in three locally produced films ("Queen of the Castle," "Sleigh Belles," and "Walter's Wedding.") She appears in the books "Legends of Drag," "Milwaukee Drag: Seven Generations of Glamour," and "Show Stoppers of the Fifth Ward."

Ruthie has been on the cover of Milwaukee Magazine, guested on podcasts throughout the country, and appeared on all Milwaukee-based TV channels throughout her career. She holds the record for appearing on the most covers of Wisconsin LGBTQ publications.

Dear Ruthie held lead roles in many Milwaukee professional theater productions, including "Whatever Happened to Baby Jane," "Torch Song Trilogy," "Vampire Lesbians of Sodom," "Die, Mommy, Die," "Scenes of Love and Death in the Third Reich," "Psycho Beach Party," and many others.

She was the first drag performer to toss out the opening pitch at a Milwaukee Brewers baseball game, and one of the only drag performers in the country to do so at a Major League Baseball game. She is the only drag performer to be named Grand Marshall of the Milwaukee Pride. Parade twice.

Dear Ruthie is the only drag queen made an honorary member of the Milwaukee Press Club. In 2009, she was formally recognized for exceptional volunteer work for the NAGAAA World Series.

In 2010, she was inducted into the SSBL Hall of Fame.

She's won "Favorite Drag Personality" twice in the Shepherd Express Best of Milwaukee Awards (2024 & 2025;) "Favorite Personality" (2016) and "Best Emcee' (2017) in the Wisconsin Drag Awards; a Shepherd Express LGBTQ Progress Award - Arts & Entertainment (2016,) and Tommy Polubinsky Possum Queen Memorial Award (1999.)

In 2023, the City of Milwaukee awarded Dear Ruthie with an honorable citation for outstanding contributions to the LGBTQ community.

Dear Ruthie continues to publish her advice column in Shepherd Express and hosts charity bingo every week at Pop in Walker's Point. Her TV show, "Camp Wannakiki," still streams on Roku, Yahoo, and Amazon Prime. Two of her songs, "Camp It Up" and "Here for Camp," are available on Spotify and iTunes.

Dear Ruthies appears as Dorothy in the annual "Golden Girls Holiday Special: A Drag Parody." Her tribute show "An Evening with Joan Rivers & Friends" and "Ruthie's Big Gay Cabaret" run at various venues throughout the city.