Bob The Drag Queen is the stage name of Christopher Caldwell, a drag performer from New York City, New York. She is one of 12 contestants who competed on the eighth season of RuPaul's Drag Race. She was crowned the winner of season eight on May 16th, 2016.

RuPaul's Drag Race

Episode One : Keeping It 100!, Bob was assigned the challenge,'Gone With The Window' from Season 2. She had to make a outfit from the supplies Bob received. Bob made Purse First on the episode. She was marked SAFE and lived onto the second week.

Season Competed Season 8
Ranking 1st (Winner)
Mini-Challenges Won 1 (Ep. 6)
Times as Team Captain 0
Main Challenges Won 3 (Ep. 3, Ep. 5 and Ep. 7)
Times in Bottom Two 1 (Ep. 8)
Episode Eliminated Not Eliminated


  • "Is Beyonce scared of Britney? Then Bob ain't scared of Derrick."
  • "Purse first! Purse first! Walk into the room purse first! Clack!"
  • "If you wanna do like memorable drag next week I can give you some tips." (to Derrick Barry)
  • "If my intentions were to hurt you, you'd be crying right now, bitch!" (to Derrick Barry)
  • "Find something about you that you like and focus on that. If I don’t like my face, if I don’t like my skin, if I don’t like my weight. I think to myself ‘I have a nice teeth.’ And it may just start with that one tooth. Look at that tooth. That’s a nice tooth, man. And then once you can accept that little thing about yourself, you can just accept you for who you are."
  • "Everything works out in the end, and if it's not working out, then it's not the end."
  • "Because I didn't eat a f*cking baby!"
  • "No one better be disrespecting me."
  • "I just wrote corn!"
  • "Why y'all gagging, I bring it to you every episode!"
  • "Taste it bitch! Expensive vodka!"
  • "as a public servant I believe in serving the people. That's why I want BJs for every single American! That's right! Better Jobs for every American! Buy yourself something pretty."


  • Bob's mother has a rare condition called "Bronchiolitis obliterans organizing pneumonia (BOOP)", a form of pneumonia that is more extreme.
  • He first started doing drag for an LGBTQ+ pride event, where he and his friends protested.
    • Doing so, he was arrested for holding up traffic with his friends.
  • His original stage name was Kittin Withawhip .
  • Bob is tied with Bebe Zahara Benet for having the worst Dusted or Busted score out of any winner, both scoring 3 in their respective seasons.



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