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Brick Wall Comedy
Brick Wall Comedy
Cover image credit: Thumbnail: YouTube · Bob The Drag Queen

Woke Man in a Dress

Bob The Drag Queen

YouTube · 2023 · 73 min

A direct and conversational stand-up hour from a drag superstar.

Watch it free on YouTube (opens in a new tab)

Bob the Drag Queen handles crowd work with the ease of a veteran schoolteacher, commanding the stage out of drag and letting his dry wit do the heavy lifting. The title comes from a real online comment calling him a “woke man in a dress,” a label he wears with pride as he leans into the generational divide and the oddities of modern culture. Filmed at Comedy on State in Madison, Wisconsin, the 73-minute set was released in June 2023. At this stage in his career, the RuPaul’s Drag Race winner was already a highly sought-after multi-hyphenate, busy co-hosting the Sibling Rivalry podcast and preparing to serve as the master of ceremonies on Madonna’s Celebration Tour. The material touches on his mother’s childhood warnings and the differences between gay men and lesbians on vacation, alongside a segment where he explains dial-up AOL and swapping CDs in a moving car to a bewildered Gen Z audience member. The special won a Webby Award in 2024 for Comedy Video & Film, and the audio version was named Comedy Album of the Year by The Interrobang.

The set list

4 bits

  1. Explaining C-sections

    Breaks down the procedure elaborately with foul-mouthed, teacher-like authority

  2. Old school internet, DVDs, and AOL

    Humorously 'oldsplains' obsolete early-2000s tech and media to younger audience members

  3. Gays vs. lesbians on vacation

    Examines behavioral and cultural differences between gay men and lesbians while traveling

  4. The definition of Pride

    Frames Pride as the one time a year extremely queer people get to feel completely normal

How it plays

Tone
Foul-mouthed, heartfelt, bold, and energetic
On stage
Straight-talking, foul-mouthed teacher in full drag; commanding, highly expressive, and unapologetically direct
Pace
Hyper-present and in utter command of the room, generating big reactions with subtle physical timing, facial expressions, and hip pops
About
Growing up Black and queer in the American South, Queer and lesbian dynamics, Celebrity and fame, Nostalgia and obsolete technology, Gender roles and femininity, Childbirth and C-sections

What the critics said

Praised for magnetic stage presence, sharp storytelling, and total command of the venue, highlighting Bob's talent as a legitimate standup comic beyond drag spectacle

In the room: Energetic club setting with the crowd kept in stitches from start to finish

Summed up from reviews, articles and listings. Sources: variety.com, standupd.com, shorefire.com, pastemagazine.com, wrotepodcast.com, letterboxd.com, en.wikipedia.org.

Backstory

Retooling of his previous special with 30 additional minutes, exploring his life as a Black queer person growing up in the deep South and adjusting to newfound celebrity

Details

Released
Taped
Comedy on State, Madison
Runtime
73 min
Where
YouTube
Topics
Before
Live At Caroline's (2020)
After
This is Wild (2026)

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