“We put out the ‘…Baby One More Time’ single in September or October of ’98, and then the album in January of ’99, and both were enormously successful.” That might be something of an understatement considering the album sold more than 25 million copies and the massive impact Britney would have on music, culture and the world at large. 

It’s hard to fathom, then, that for her first tour Spears performed at malls across the country with just two back-up dancers. “We were like, if we take Britney to the malls, which is where America lives, and they see her, they’ll connect with her,” Rudolph says. “I remember going to one of these shows at Macy’s Herald Square in New York. We were performing in the middle of the Calvin Klein section and there were underwear racks around us. People were just shopping and not realizing that 10 feet away from them was Britney Spears, who was about to become the biggest star in the world.” 

But finding the right milieu for that gift, in this day and age of over-heated touring markets and mega-festival, is no easy feat for an artist of Spears’ caliber in the throes of motherhood yet still in her prime – that’s where Rudolph’s and Light’s expertise and foresight came into play. 

“I had been spending quite a bit of time in Las Vegas and seeing a big transition in the demographic patterns,” says Rudolph, who early on recognized a new, emerging Sin City market. “It was moving away from the traditional middle-aged couple getting dinner, seeing a show, doing a little gambling and going to sleep, and moving towards a much younger person with a very different reason for being in Vegas.”

The pathology for this emergent demo of 20- and 30-somethings, according to Rudolph, was different: They check into the hotel, make a beeline for the pool where they drink, party and listen to DJs; return to their room, order room service (instead of going out to restaurants) and take a disco nap; then wake up at 11 p.m. and club the night away without ever hitting a gaming table. Team Britney’s vision was to break into that pre-clubbing time.  

While identifying an emerging market isn’t easy, harder still is convincing others to invest in your vision. Fortunately, Light, who’s booked Vegas “forever,” with such artists as Bette Midler and Shania Twain, got it right away. “When we were talking about what was the next live move for Britney, Larry – who truly is one of the great managers – and I talked about going to Vegas and what that would look like,” Light recalls. “We reached out to a bunch of properties, and the first responses – and remember it wasn’t like it is today – were lukewarm at best. It certainly didn’t fit the model at the Colosseum, there was no Park Theater, and the only other room was at Planet Hollywood.”

“It was a white elephant,” Rudolph says of the underutilized Planet Hollywood theater, which seated 7,000. “When I walked in there, it was dusty and looked like shit. I basically said, ‘Hey, this looks like it hasn’t been touched in 40 years.’ And they basically said, ‘Well that’s because it hasn’t been touched in 40 years.’ So I said, ‘Alright, the only way we’re going to do this theater and do this new show is if we do get some money for capital improvements.” 

Caesars also saw the vision. “The CEO was Gary Loveman, who was a really bright guy,” Light recalls. “He made a bet that this was gonna work and put $20-something million into this theater. 18 months later you couldn’t get a date in the room. It was booked out for two years.”

“We invested heavily into the production,” Rudolph adds, “for a show in a 4,400-seat theater. And we built it the right way. We made it spectacular.” This included having Baz Halpin (whose clients have included Taylor Swift, Pink, Black Sabbath and Katy Perry) as creative and stage director for the show, Marco Morante as the costume designer, and a 360-degree video wall.

Light compares the show to a more historical antecedent. “Think back to Donn Arden’s ‘Jubilee,’ without the showgirls and huge headdresses of the old days,” he says, “but it was taking those big production shows and bringing it into the 21st century for that audience and done just brilliantly.”

“Here’s what I remember about the first night more than anything,” Light continues. “When she came out, everyone stood up, which was unheard of for a Vegas show. It was a party from the second it started. I was surprised because I’m so used to a Vegas audience sitting in their seats and being like, ‘Entertain me.’ It was not that.”

So what do Lady Gaga, Dave Chappelle, Bryce Harper, Danica Patrick, Bobby Flay, Sofia Vergara and Joe Manganiello, Shania Twain, Nasim Pedrad, Peaches, Jeff Dunham, Jeremy Scott, Julianne Moore, Nuno Bettencourt, Minka Kelly, Melissa Joan Hart, Tamar Braxton, Skrillex, Abby Wambach, Arnold Schwarzenegger, Miss USA Nina Sanchez and the late Florence Henderson have in common? Not much, really, but they were among the million ticket holders clamoring to see Britney’s “Piece of Me” Vegas residency.

“One night I was standing with Britney backstage,” Rudolph recalls, “and I was walking her to the stage, and as I literally said goodbye to her I said, ‘Oh, and Jay-Z and Beyoncé are sitting in the front row.’ She said, ‘No! What!? Why didn’t you tell me? I can’t go out there.’ And I go, ‘That’s why I didn’t tell you. I didn’t want you to have time to think about it, now just go out and perform.’ And she was like, ‘You motherfucker,’ with a smile on her face. And then of course, she went out and Jay and Beyoncé are sitting right there. And Dave Chappelle was there that night also. But that’s the way it rolled. Everybody wanted to see it.”

After the close of the show on Dec. 31, 2017, Spears embarked on the “Piece of Me” summer tour for a number of reasons. “Number one,” says Rudolph, “we were done with the show, and she had an entire year off. And she wanted to do something. So we spoke about it. A lot of people on the East Coast and in Europe didn’t get to come see the show. because not everybody has the ability to get on a plane and come to the West Coast.” 

And as CAA’s Light pointed out, the majority of the show was already built. “Think about the cost of just building a stage and rehearsing it,” he says, “that’s a big part of the cost. We didn’t take the exact show from Vegas, you never could because it was built into a theater, but we took a lot of those elements, so the show was built and rehearsed, so the normal costs that get amortized were gone.”

While the tour set records in disparate locales between its trans-Atlantic venues, Rudolph recalls one show in particular: “She loved playing at Radio City,” he says. “And it’s funny, because I reminded her when we got there. ‘You know what happened the last time you were here?’ She said, ‘No, what?’ I said, ‘You kissed Madonna.’ And she started laughing and said, ‘Oh my God, I’m going to say something about that when I go out there.’ And she did and it was really cute. She said something like, ‘Hey everybody, guess what I did last time I was here?’ The audience paused, and she said, ‘I made out with Madonna.’” 

The “Piece of Me” tour set records from the Sands Bethlehem Event Center to Brighton, U.K.’s Preston Park to Göransson Arena, Sweden, where it broke a long-held record held by the Scorpions. The tour is also up for a People’s Choice Award. All of which brings us to her just-announced new residency at the Park Theater, which Team Britney is hard at work putting together. 

“We just had our first full session yesterday with NappyTabs for a few hours yesterday morning,” says Rudolph referencing Tabitha and Napoleon D’umo of Funky Monkey Productions, the new residency’s creative directors who not only developed lyrical hip-hop dance but worked on “So You Think You Can Dance,”  “America’s Got Talent,” and Jennifer Lopez’s “All I Have” residency, in addition to other productions. 

“We went through our first draft of creatives, We sat down, spitballed ideas and Britney came up with a million of them. They came up with a million ideas. We have a tentative title, narrative, visuals, set lists and everything right now. But it’s far too early to talk about it. I can tell you this: It’s going to different from the ‘Piece of Me’ show. It’s going to be a little bit more street. A little bit more rhythmic. It’s going to feel a little cooler. But it’s still going to be a classic Britney great hits show. You’ll know every song, the visuals will be incredible, she’ll be at 110 percent in terms of her performance. You’re going to have amazing dancers, costumes, set pieces, video, sound – amazing everything.” 

But beyond all of Spears’ topnotch production values, strong content and universally-lauded performances, the crux of what connects her to legions of fans who flock to Vegas is something far more visceral, personal. “To a huge swath of a generation Britney represents something incredibly important to their lives,” Light says. “Her performance takes them back and makes them feel great. She connects on that level.”