Thu. Apr 30th, 2026

Bob the Drag Queen Says ‘Exhausting’ Madonna Travel Is ‘Worth It’

A typical day for Bob the Drag Queen on Madonna’s Celebration Tour begins with post-travel R&R.

“Travel can get exhausting, but it’s worth it when I’m able to live out my dream in front of thousands of fans each night,” the RuPaul’s Drag Race season 8 winner, 37, exclusively shared in the latest issue of Us Weekly.

Bob (real name Christopher Delmar Caldwell) has joined Madonna at several Celebration Tour dates since it kicked off in October 2023. On this particular day in the life, Bob geared up for a performance in Sweden by enjoying some alone time after exploring Stockholm.

“After going for a 30-minute walk in the city, I unpack and make myself comfortable in [my] hotel room,” Bob told Us.

Once at the concert venue, Bob gets ready for the show. “I exclusively use my beauty brand BOMO’s eye shadow palette Pretty/Funny to transform into one of the daintiest women you will ever see,” the TV personality shared.

Scroll down to follow Bob through a day in the life:

8:42 a.m.
Bob arrived in Sweden, where he served as the special guest at Madonna’s Stockholm concert. 
Courtesy of Bob the Drag Queen
9:14 a.m.
“Since I’m away from home for most of the year, I bring recording equipment for when inspiration hits,” Bob told Us of his travel essentials.
Courtesy of Bob the Drag Queen
1:24 p.m.
Giving them something to talk about! The podcast host recorded an episode of the award-winning “Sibling Rivalry” with Bob’s “sister and nemesis,'” Monét X Change: “We spend two hours debating really important trending, relevant, hot-button issues.”
Courtesy of Bob the Drag Queen
4:36 p.m.
Once soundcheck was complete, Bob begins used BOMO Beauty products to get glam for the show — a process that can take up to four hours! 
Courtesy of Bob the Drag Queen
8:47 p.m.
Showtime! “Each night, I kick off [the] show by parading through the crowd of over 20,000 fans while taking them on the journey of Madonna’s career by telling stories, jokes, dancing, lip-syncing, and emceeing,” the comedian told Us.
Courtesy of Bob the Drag Queen
12:00 a.m.
The hustle never stops: “It may seem crazy, but after the show you can find me back at the hotel recording a YouTube video — because I am a Queen for the people!” Bob shared. “Today’s video was a review of my seventh Drag Race audition tape.” Then, it was off to bed!
Courtesy of Bob the Drag Queen

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By Michael

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