[3] 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.

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.

"[11] 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.

He explained that he "became obsessed" with the show and it immediately inspired him to order a TK-7 makeup kit from 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.

[15][10][16] His initial stage name was Kittin Withawhip, which was a reference to Kitten with a Whip (1964), a film that starred Ann-Margret.

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).

[20] On the season's eighth episode, Bob "lipsynced for her life" against her rival Derrick Barry and won.

[22] In 2020, he began co-hosting We're Here on HBO alongside fellow Drag Race contestants Eureka O'Hara and Shangela.

[27][28] In 2016, shortly after winning Drag Race, Bob released the single "Purse First" featuring DJ Mitch Ferrino.

[31] 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.

[33] Bob played the role of Belize in Berkeley Rep's production of Angels in America from April to July 2018.

[40] Her TV comedy special, Bob the Drag Queen: Suspiciously Large Woman, aired on Logo in July 2017.

[43] Bob also writes jokes for other drag queens including Trinity the Tuck, Ginger Minj, and Monét X Change.

In June 2024, Bob was announced as a contestant on the third season of the American reality competition The Traitors.