At 36 years old, Bob The Drag Queen has this physical status:
In the summer of 2009, Caldwell started doing drag, after watching the first season of RuPaul's Drag Race on TiVo. He explained that he "became obsessed" with the show, and it immediately inspired him to order a TK-7 makeup kit off of the Ben Nye website. Since his first presentations, his character was focused on stand-up comedy routines, and he started lip-syncing after a couple of months into his drag. His initial stage name was Kittin Withawhip, which was a reference to Kitten with a Whip (1964), a film that starred Ann-Margret. He was featured in Leland Bobbé's Half Drag Series with his name. In his early drag career, Caldwell would perform with a nine-foot bullwhip.
In the beginning of his career, Caldwell faced challenges as a drag queen. As he described, "It did not make me money or get me gigs. It cost me a lot. I did this competition every Thursday. Then another one on Wednesday. And another on Tuesday. I never won any of them. Ever. After a few years, I finally won one. It was really addictive and fun doing competitions."
In 2013, Caldwell officially changed his stage name to Bob the Drag Queen. As he explained, at a karaoke hosting gig, "The guy goes, 'Give it up for your host... Kate. But she made light of the moment, reintroducing herself as 'Kate the Drag Queen,' then 'Kim the Drag Queen' throughout the evening. Then at the end of the night, I was like, 'Give it up for... Bob the Drag Queen.' And I was like, 'That sounds really funny.'"
On February 1, 2016, Bob the Drag Queen was revealed as a cast member on the eighth season of RuPaul's Drag Race. On the show, he was noted for his focus on comedy. During the show, he won three challenges, including the recurring "Snatch Game" (where he portrayed Crazy Eyes, as played by Uzo Aduba, and Carol Channing). On the season's eighth episode, Bob "lipsynced for her life" against Derrick Barry and won. On May 16, 2016, Bob was crowned the winner of the season and received a cash prize of $100,000.
In June 2019, a panel of judges from New York magazine placed Bob eighth on their list of "the most powerful drag queens in America", a ranking of 100 former Drag Race contestants.
In 2020, he began co-hosting We're Here on HBO alongside fellow Drag Race contestants Eureka O'Hara and Shangela. In the series, the trio of drag queens travel across the United States to recruit small-town residents to participate in one-night-only drag shows. After premiering on April 23, 2020, the series was renewed for a second season, which premiered on October 11, 2021. In December 2021, the series was renewed for a third season. The series has received acclaim from critics.
In 2016, shortly after winning Drag Race, Bob released the single "Purse First" featuring DJ Mitch Ferrino. Also in 2016, he appeared in the music video for MC Frontalot's "Mornings Come and Go". He also collaborated with Alaska Thunderfuck on the single "Yet Another Dig" in 2017, and contributed to the compilation album Christmas Queens 3 (2017). He collaborated with Shangela for a Christmas theme song, "Deck A Ho" in December 2017.
On March 15, 2018, Bob debuted the podcast Sibling Rivalry with his drag sister Monét X Change as co-host and produced by DJ Mitch Ferrino. On April 2, 2018, a video version of the podcast was uploaded to YouTube.
Bob appeared as a guest co-host alongside Trixie Mattel on The Trixie & Katya Show, filling in for regular co-host Katya during her hiatus. Her TV comedy special, Bob the Drag Queen: Suspiciously Large Woman, aired on Logo in July 2017.
Bob played the role of Belize in Berkeley Rep’s production of Angels in America from April to July 2018.
In November 2019, Bob was interviewed by KMVT about a one-time drag event hosted in Twin Falls, a show highlighting local drag queens and introducing international drag talent to Magic Valley. This event was filmed as part of Tidicue's HBO show We're Here (2020).
Bob's second comedy special, Bob The Drag Queen: Crazy Black Lady, aired on OutTV in Canada in 2020.
Bob also writes jokes for other drag queens including Trinity the Tuck, Ginger Minj, and Monét X Change.
In March 2020, Bob performed alongside fellow drag race alumni BeBe Zahara Benet, The Vixen, Monique Heart, Peppermint, and Shea Couleé in the Nubia tour, a live drag show featuring and produced by Black drag queens.
Bob is a co-founder of Black Queer Town Hall along with Peppermint. The inaugural event featured speakers such as Laverne Cox and Angela Davis and raised over $150,000.
In May 2021, Bob was featured in Coach New York's "Pride is Where You Find It" campaign.
Bob is an LGBT activist and spoke on RuPaul's Drag Race of a moment when he was protesting for LGBT rights and was arrested in drag.
Bob is the drag mother of Miz Cracker and drag sister to Monét X Change, who placed fifth and sixth, respectively, on season 10 of RuPaul's Drag Race, with X Change going on to win RuPaul's Drag Race All Stars season 4 and Cracker placing as runner-up on RuPaul's Drag Race All Stars season 5.