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Bob (out of drag) with her drag daughter Miz Cracker

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.

Bob has had a large career post drag race releasing dance singles, playing Kitten in the Netflix movie Cherry Pop, and releasing her own comedy special Suspiciously Large Woman.

Bob also has a show on WOWPresents Plus called BOBin' Around which follows her and her assistant Luis as they travel around the world.

Starting in 2018, Bob has been filling in for Katya on The Trixie & Katya Show as of the 10th episode.

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 an 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

Memorable Quotes

  • "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 fucking baby!"
  • "Art."
  • "No one better be disrespecting me."
  • "I just wrote corn!"
  • "Why y'all gagging, I bring it to you every episode!"
  • "I know y'all ain't starting this WHITE ass party without me.."
  • "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."
  • "Than why did I waste my time putting on thissssss, (dramatically removes coat showing off glitter extravaganza) Ow wait there's more... THIISSSSSSS!"
  • "THAT'S MY BABYYY!" (to Miz Cracker)
  • "Is the train still runnin'?"


  • 1493237139-bob the drag queen tickets temp
    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’s drag daughter is Season 10 contestant Miz Cracker.
    • Bob helped Miz Cracker get into drag for the first time, as they had never done drag before. 
    • Ironically, Bob is younger than her drag daughter.
  • Bob’s drag sister is Monét X Change, who also competed on Season 10.
  • Bob is the 1st and only contestant ever to impersonate two celebrities in a single Snatch Game performance, impersonating Uzo Aduba's Orange Is The New Black character, Suzanne "Crazy Eyes" Warren, for the first half of the game and switching to Carol Channing for the second half.
  • Bob played a character named "Kitten Withawhip" in the movie "Cherry Pop". The movie also featured Detox, Mayhem Miller, Tempest DuJour and Latrice Royale
  • Bob is the only winner to never be placed in the top in an episode without winning the challenge.
    • He is also the longest-lasting contestant to never place high or low during their run on the show, as he either won, was safe or was in the bottom two for all eight episodes of his season.
    • His drag mother is Peaches Christ.



Best of Bob the Drag Queen

Best of Bob the Drag Queen

Vote for Bob the Drag Queen

Vote for Bob the Drag Queen

Bob the Drag Queen's 'I Don't Like To Show Off' Performance

Bob the Drag Queen's 'I Don't Like To Show Off' Performance

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