With a $1 million insurance policy on his member, Keiran Lee is known for his magical penis. But the legendary Brazzers talent/producer often has to remind people of what he doesn't have.
A magic wand.
Week after week—for more than a decade—Lee has given the same answer to aspiring adult stars who contact him in hopes of shooting the first scene of their career for Brazzers, the most prominent studio in porn.
"I tell them It's not that easy," Lee says. "It's almost impossible for me to get them on the site when they're brand new. They have to work their way up."
Lee pauses.
"Well," he says, "most of them do."
Indeed, every so often, a unicorn gallops into vision, a can't-miss prospect who doesn't need to "pay her dues" by shooting for Brazzers sister sites such as MoFos and Reality Kings. When stardom is certain, Lee says, why not start at the top?
"It's rare, but sometimes you see a girl that clicks all the boxes, and you just know," Lee says.
"Sinatra Monroe was one of those girls."
Ah, yes, Sinatra Monroe—the former exotic dancer from Tampa who is quickly becoming one of the industry's newest "it" girls.
Lee sensed the potential as soon as he glanced at the pictures Monroe texted him last summer. Not only could he not find a flaw, but Lee realized Monroe possessed physical attributes that would put her in a class of her own if she joined the industry.
While plenty of porn stars can match her 38D breast size, few—if any—boast a backside as ample and firm as Monroe's picturesque posterior. Even more striking are the wavy crimson locks that cascade past Monroe's shoulders and down her back. Brazzers executives aren't big on ranking talent, but if there's a hotter redhead in the business, well … they want to see her.
"There's no one in the industry like Sinatra," Brazzers director Lea Lexis says. "She's a unique beauty."
That's why studio executives didn't balk when Lee announced last August that he'd invited Monroe to make her career debut in a threesome scene with Elizabeth Skylar and Manuel Ferrara. Playing a stepdaughter who seduces a delivery man along with the help of her stepmom, Monroe crushed the dialogue and acting portion of the shoot. And once her Daisy Dukes and tank top came off and the sex began, Lee was floored. The rookie fucked like a veteran.
"Her performance style matches her hair," Lee says. "She's a firecracker."
Monroe, who turned 28 in June, still remembers the flood of emotions she experienced as she drove away from set that afternoon.
"I loved it so much—and I knew, at that moment, that this was where I belonged, that this was the career for me," Monroe says. "I kept thinking, 'I hope they liked me. I hope I impressed them. I hope they call me back.'"
Brazzers certainly has.
Time and time again.
One year later, Monroe has shot 18 scenes for Brazzers and other Aylo brands and 14 more for A-list studios such as Blacked Raw, Jules Jordan and Team Skeet. Even more impressive is that Monroe—who is represented by agent Mark Spiegler—has already amassed nearly 350,000 followers on Instagram.
That number may be jarring to some—but not to anyone familiar with Monroe's past. While her stunning appearance may be her most glaring attribute, the native Floridian has always used a different trait to earn not just attention, but respect.
"I love to work," Monroe says. "I embrace it. I enjoy it. Ever since I was a little kid, I've always been a grinder."
******
As she removed the wad of $10s and $20s from her pocket and began to count, Sinatra Monroe could hardly contain herself. It was the spring of 2017, and the 20-year-old had just earned $500 on her first shift as a stripper at The Penthouse Club in Tampa.
Monroe had actually been hired as a waitress at the gentlemen's establishment one week earlier, and the owner made a prediction when he gave her the job.
"Eventually," he said, "you'll want to dance."
Monroe chuckles about it now.
"I lasted seven days as a waitress," she says. "I'd take drinks into the VIP rooms and see how money those girls were making and think, 'I want to make that much, too.'"
For Monroe, a job in the sex industry was a natural fit.
She began watching porn at a young age—"probably too young," she says—and was making out with girls by her early teens. "I was born bisexual," says Monroe, who often got busted sneaking out of her house in the middle of the night to hook up with guys. When Monroe lost her virginity, she was the one who pressed the issue with her boyfriend.
"My girlfriends and I were always looking up (porn) videos on the internet, stuff we were curious about," Monroe says. "I've always been a very sexual person down to my core."
Monroe had no idea where life would take her as she neared graduation. She'd shown promise in the performing arts, excelling in ballet in her early teens before focusing on musical theater in high school, when she starred before the student body as Alice in "Alice in Wonderland."
Still, as much as Monroe enjoyed being on stage, she never considered turning the hobby into a career.
"My high school teacher would get so frustrated," Monroe says. "She was like, 'If you just took this seriously, you'd go so far.' Instead, I was the kid who was sneaking out during lunch, smoking a doobie with friends and getting Taco Bell. I was not a 'school person' at all."
If anything, Monroe's passion was money and finding ways to earn it. Monroe jokes that she's been a hustler ever since starting her own babysitting business at age 12, so perhaps her parents shouldn't have been surprised when she told them that, despite the funds they'd set aside for tuition, she had no interest in going to college.
Instead, Monroe became fully absorbed in the restaurant industry, starting as a host at a fine dining establishment before hopscotching from one waitressing job to the next. She served pasta at Nabruzzi Trattoria, wings and beer at Marlow's Tavern and steak and sushi at Grille 54. At each stop Monroe strived to be the hardest worker on staff.
"If anyone offered to give up a shift, I was the first one to raise my hand," she says. "I was always like, 'I want to work! I want to make money!'"
The same day she was hired at Grille 54, a co-worker took one look at Monroe and suggested she apply at The Penthouse Club. The $200-$300 she made each night serving food would seem like peanuts to the money she'd earn at a gentlemen's establishment.
Monroe took the advice and began working both jobs. It wasn't uncommon for her to wait tables til 8 or 9 each night before taking the floor at Penthouse around 10 or 11.
Slithering across the stage to music by T-Pain and eye-fucking smitten customers throughout the room, Monroe quickly became one of the highest earners at the club. For the first time in her life, she felt like she'd found her calling.
"I never learned any of the crazy tricks," Monroe says, "but I knew how to move my body and shake my butt, and that made me a lot of money.
"I was the girl who would make eye contact with you and wave you over to the stage. The key is to flirt on the stage and have interactions, so when you get off that stage, the guy is like, 'I wanna hang out with her!' It came very naturally to me."
After a few weeks, Monroe was doubling and tripling the $500 she made on her first night. Eventually, a friend suggested she travel to Las Vegas, where dancers from across the nation flock to make big money at some of the nation's most well-known strip clubs.
Monroe blended in seamlessly, and before long, she found herself living in Sin City for months at a time. Commanding the stage and VIP rooms at Sapphire, Monroe was raking in cash like never before. Events like the Super Bowl and March Madness—which lure thousands of visitors to Vegas—helped Monroe's monthly earnings skyrocket to more than $30,000.
"Vegas is a totally different ball game because there are so many girls working in the club," Monroe says. "It's hard to make money if you're not aggressive. Guys are there to spend money, get wasted, and have fun with you. That's what you're there to provide for them. You have to go up and be bubbly as hell, have a good time, and party with them.
"I told girls all the time, 'You can be beautiful, but if you don't know how to talk to these guys and have a conversation with them and sell yourself, you will not make money. That's what it's about.' I've always been good at selling myself."
Vegas is also where Monroe developed the stage name that sticks with her today. In Florida she danced as Sasha or Scarlett. But when she learned those names were taken at Sapphire, Monroe remembered passing by "Sinatra St." earlier that evening on her way to work.
"So I went with it," she says. "Guys loved it. They were like, 'That's interesting. It's different. I like it.'"
After dancing for four years, Monroe's career hit a snag when the COVID pandemic forced clubs to shutter in March of 2020. She moved back to Tampa and reconnected with the owner of Grille 54, who was looking to capitalize on the cannabis craze by opening a business in Oklahoma. He offered Monroe a job in sales, and before long, she found herself living in Tulsa.
Day after day, Monroe would visit dispensaries and hawk edibles, flowers, and tinctures. The business boomed to the point that Monroe decided to become an investor.
Goodness knows, she certainly had the funds.
Along with the money she'd earned over the years as a dancer, Monroe began experiencing success as an OnlyFans creator during her free time in Oklahoma. Even though most of her content was limited to photos and solo shoots, Monroe watched her income elevate from $2,000 to $8,000 monthly while her Instagram following soared to 85,000.
Not bad for someone with zero mainstream exposure.
Still, after two years in Tulsa, Monroe knew it was time to take the next step.
So she reached out to Keiran Lee.
******
Moments before their shoot last August, Sinatra Monroe and Elizabeth Skylar were approached by a Brazzers executive as they sat in their makeup chairs.
"He was like, 'By the way, this is going to be an ad scene,'" Skylar said. "Sinatra and I looked at each other and went, 'Holy shit! This is a big deal.'"
Indeed, as if the anxiety surrounding the first scene of her career wasn't enough, Monroe now had the added pressure of knowing the footage would be pushed and advertised throughout all of Aylo's platforms and also on PornHub.
"She was nervous," Skylar says, "but once the cameras came on, she acclimated very quickly. She knew what she was doing. I was shocked it was her first scene because it felt very organic."
Viewers agreed, as "Wife and Stepdaughter Want Delivery Guy's Package" ranked as one of Brazzers' top ad scenes of 2023. The feedback had to have been satisfying for Lee, the producer who gave Monroe her big chance.
"As soon as the guys in the main office saw it, they were like, 'Let's get this girl in for a lot more scenes.'
"I've been with Brazzers for 18 years. I know the type of girl that the fans really appreciate, the Phoenix Marie's, the Nicolette Shea's. I looked at Sinatra and thought, 'She clicks every box that those girls click.'"
Monroe's appearance is certainly her calling card, and she takes pride in it, especially since it takes so much discipline to maintain.
Monroe has been a workout addict since she began dating a trainer at age 16. She goes to the gym five-to-six times a week, focusing less on cardio and more on lifting weights. Each session is devoted to a different muscle group, and Monroe designates two days a week to her lower body. It takes a lot of work, after all, to maintain that perfect butt.
Monroe drinks a gallon of water daily to help with her glow and complexion. A natural blonde, Monroe began dying her hair about two years ago, starting first as a brunette before dabbling in various shades of red.
"I definitely think being a redhead gives me a bit of an edge," she says. "I'm very happy with this shade. I don't see it changing anytime soon."
Lexis says Monroe's effort to maintain her appearance doesn't go unnoticed.
"Sinatra takes great care of her body and hair and skin," Lexis says. "She has a self-care routine that puts her ahead of a lot of other models. Considering we shoot such high-quality video, those things are important.
"When you couple her pretty hair with her complexion and her pretty (hazel) eyes, it's not something you run across every day. It makes her special."
Still, Lexis stresses that Monroe's impressive qualities extend far beyond her beauty.
"There's a presence about her that's very elegant," Lexis says. "You see it in the way she carries herself. Even though she's more on the sporty side, she has a vibe, an energy she gives off when she enters a room that makes her a star."
From the get-go, Monroe has also proven to be an elite performer, using eye contact and dirty talk to melt viewers and scene partners alike. Along with Ferrara, Monroe has already shot with high-profile stars such as Mick Blue, Ricky Johnson and Zac Wild. And she recently filmed an OnlyFans collab with iconic star Johnny Sins.
"I was like, 'Oh my God! Now I see what the (hype) is about,'" Monroe says of Sins. "He was so passionate, great eye contact … he really gives his all for a scene."
Lexis says Monroe's work has been well-received because it feels so genuine. Monroe makes it a point to develop chemistry with her co-star long before filming begins.
"She knows what it takes to make a good scene, which tells she's very intelligent," Lexis says. "She understands that chemistry is needed. When a talent puts in the effort to establish that connection, you can tell on camera. It makes for a better product."
Just one year into her career, Monroe realizes she's still a work in progress—and she's also still learning more about herself sexually.
Monroe has discovered how much she loves boy-girl-girl threesomes, adding that her Brazzers scene with Ricky Johnson and Scarlett Alexis is among the best of her young career. She's also developed a newfound fondness for rimming.
"Some guys are soooo into it and grateful for it," she says. "That's hot to me. It's the same thing as going down on a woman—if they get off, I'm happy. I'm a pleaser at heart."
Monroe says anal scenes are likely in her future, but she's certainly not in a rush. She's pleased with the pace of her career thus far and wants to continue the steady climb. Monroe still resides in Tampa but travels to Los Angeles monthly for shoots and usually stays for 7-10 days.
"It gives me a mental break," she says of her routine. "It allows me to be in my peace and my serenity in Florida. I'm not the type to say 'no' to work, so if I lived in LA, I know I'd get burned out."
That's the last thing Brazzers would want to happen.
Lee suggested Monroe has the potential to become a contract star. And Lexis said the popularity of her scenes continues to soar.
"We do a lot of research," Lexis says. "Our members love her and, and our team thinks she has a bright future. We're going to keep on shooting her and shooting her. What you've seen is only the beginning."