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."
1986
Christopher Delmar Caldwell, known by his stage name Caldwell Tidicue, and better known as his drag name Bob the Drag Queen (born June 22, 1986), is an American drag queen, comedian, actor, activist, musician, and reality television personality.
He is best known for winning the eighth season of RuPaul's Drag Race.
Christopher Delmar Caldwell was born to Martha Caldwell on June 22, 1986.
His last name, "Caldwell", was later incorporated into the professional name "Caldwell Tidicue".
He was born in Columbus, Georgia.
He moved a lot as a kid, which included Phenix City, Alabama, Corinth, Mississippi, LaGrange, Georgia, and Atlanta, Georgia.
He was raised in Clayton County, Georgia.
Caldwell explained, "You can call it the hood. You can say it. That's where I'm from."
His mother owned a drag bar in Columbus, Georgia.
On the nights that she could not afford a babysitter, she brought Caldwell to the drag bar, where he would work and collect money from the patrons.
Caldwell has described his mother as a supportive early influence on his life.
He explained, "I also grew up with a mom who told me I could do anything, so I was like, 'Y'all don't even know how I am.' My mom was one of the moms who was like, 'You are so handsome why aren't you modeling? I am handsome, but model... let's not get crazy."
Bob has also been influenced by several other drag queens, such as Peppermint, Bianca Del Rio, BeBe Zahara Benet, and her Sibling Rivalry co-host Monét X Change.
As a teenager, Caldwell attended Morrow High School in Ellenwood, Georgia.
He then went back to Columbus to study chemical engineering at Columbus State University.
2008
He first appeared in drag when he attended a lesbian party during Pride Month 2008.
When Caldwell was 22 years old, he moved to Queens, New York, with $500 and two suitcases.
He originally intended to become an actor and standup comedian.
Before becoming a drag queen, Caldwell worked in children's theater for years and "always found children to be a source of joy for [him]."
2009
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.
2013
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.'"
2016
After Drag Race, he pursued acting, appearing in television shows such as High Maintenance (2016), Tales of the City (2019), and A Black Lady Sketch Show (2019).
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.
2019
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.
2020
As of 2020, he has more than one million followers on Instagram and was the first Black Drag Race queen to reach the milestone.
In 2020, he began co-hosting We're Here on HBO alongside fellow Drag Race contestants Eureka O'Hara and Shangela.
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.
