It is early Saturday evening and the fast-talking, million-dollar gambler is on a roll as he makes his way to a friend's party in Los Angeles.
Throughout the drive, weaving though the city's traffic, Cipriani is on his phone telling me the wildest tales - eye-watering six-figure bets, $65m private jets, high-roller groupies, celebrities, sporting superstars and stratospheric $30,000-a-night suites in Las Vegas.
Cipriani now lives beachside in Santa Monica, California, but his bombastic voice comes down the line still laced with a Philadelphia accent, the hometown he grew up in.
Philly was where Cipriani learned his trade from a bunch of "older degenerate gamblers" who took him under their wings, dragging the-then young teen into Atlantic City's famous casinos and racetracks dotted around the east coast.
'Casinos will send $65m private Gulfstream jets to come and pick me up,' RJ Cipriani says. Las Vegas casinos will do anything and everything to lure big-betting high-rollers on to their gambling floors. (Supplied)
Cipriani should have been inside the party 30 minutes ago, but, instead, he is parked up outside with his Brazilian wife, model and actress Greice Santo, lifting the lid on the rarefied and secretive world of whales and high-rollers in Las Vegas.
Talking to Cipriani can be like riding a rollercoaster; it's fast, exciting and can leave you dizzy. Now, sat in his parked car, Cipriani is in full flow. Party or no party, he's not stopping.
"The only reason I'm telling you this is to set the record straight," Cipriani explains to me.
Cipriani is taking aim at "that scumbag" Stephen Paddock, the mass murderer who took up a deadly sniper position on the 32nd floor of the Mandalay Bay hotel in Las Vegas and shot dead 59 people, injuring hundreds more.
In the aftermath of the massacre it emerged that Paddock, a retired accountant who had reportedly made several millions in the real estate game, liked to play poker in Las Vegas.
Casinos apparently rated Paddock a $25,000 - $50,000 player. That was Paddock's sweet spot, an amount he would win or lose in a typical sitting. And it turned out the Mandalay Bay had "comped" room 32-135, a $1000-a-night suite, to Paddock. The world's media quickly labelled Paddock a high-roller. It sounded good and read well, but it was wrong.
"He was never a high-roller," Cipriani says of gunman Paddock. "It's false reporting."
RJ Cipriani's wife, Greice Santo, prepares to board a private jet headed for Las Vegas. (Supplied)
RJ Cipriani hanging out Andrew Dice Clay, American comedian and actor, in Las Vegas. (Supplied)
Cipriani is not shy about clearing up any confusion.
"That suite Paddock got at the Mandalay is what we high-rollers call a room," he says.
"High-rollers don't get suites. We get monster suites that cost $30,000 a night."
Making his case, Cipriani speeds through a list of the ultra-exclusive and luxurious rooms in Vegas’s most prestigious hotels where he has stayed for free, courtesy of his high-roller status, alongside the rich, famous and powerful.
"I'm talking huge 800 square metre, five-bedroom suites, formal dining rooms, TOTO designer toilets in every one of the suite’s 10 bathrooms and the most unbelievable views over the city."
Your hotel neighbours, Cipriani reveals, are megastars like Mariah Carey, Oprah Winfrey and retired basketballer Michael Jordan, himself famed for being a big-time gambler. Amenities in these expansive suites are excessive, and some border on the ridiculous - perfect for Vegas.
Cipriani tells a story about inviting British boxer Lennox Lewis, the former undisputed heavyweight champion, to the penthouse he was staying at the very top of The Augustus Tower at Caesars Palace.
Former undisputed heavyweight champion Lennox Lewis was stunned by the tricked-out suite, RJ Cipriani says. (Getty)
"We'd run into each other a couple of times and I invited Lennox to hang with me. It took about three invites before he trusted trust me. I said, 'dude, why are you worried about me? I'm a skinny white guy and you're the former heavyweight champ of the world. Why are you scared of me?'"
After entering the vast penthouse, Lewis walked around, admiring the huge fish tanks, private swimming pool, king-size billiards table and multiple bars.
The British fighter then floored his host with a simple request: Lewis asked if he could take some pictures to send his wife because the uber-lux penthouse was "so unbelievable".
"I said, 'wait a minute, wait a minute. You're the heavyweight champion of the world. You mean to tell me you've never seen this kind of room before?'"
Cipriani says the exchange left him shocked. It underlined the level of privilege bestowed upon high-rollers in Vegas.
The MGM Grand, home to The Mansion, where high-rollers rub shoulders with the rich and famous. (Supplied).
Behind the locked gate lies The Mansion at the MGM Grand. 'I stayed at The Mansion, the most exclusive place in Vegas, for a month straight, and was beating them consistently every day. They finally asked me to leave,' Cipriani says.
Las Vegas is a town that loves its celebrities but - bar a select few - they just don’t gamble big. In Vegas it's the high-rollers who are literally given the keys to the city. Size matters in the gambling mecca and Cipriani is a whale - casino parlance for the industry's most prized players, those who bet huge, and can win or lose huge.
Like Captain Ahab, every casino wants to land their Moby Dick. With private jets as a starting point, casinos do everything they can to lure whales into their properties.
Hooks are baited with a set of comps, which are carefully outlined on a document called a "deal point memo". The deal point memo, negotiated between gambler and casino, is the high-roller's equivalent to a musician's rider - a performer's very particular set of requests or demands.
"There are casinos that will give high-rollers deals beyond belief just to come there," Cipriani says.
A true high-roller, such as Cipriani, must post a million dollars or more at the casino's cashier cage on arrival.
Unlike a lot of players, Cipriani says he doesn't do credit. He prefers to pay in cash.
"Two million in hundred dollar bills fits in one duffel bag," Cipriani explains matter-of-factly. "It doesn’t actually take up a lot of space."
Cipriani grew up above a barber's shop in Philadelphia, and sold pretzels before becoming a pro gambler. He says paying with cash gives him respect for the value of the money.
"I just like to feel the realness of how much you have when you come in and how much you have when you leave," Cipriani says.
"As a gambler you can't lose sight of that. The only way to do that is with cash. A bank cheque with numbers on it or a bank wire just doesn't feel the same mentally."
RJ Cipriani with former heavyweight champion Muhammad Ali, one of the most significant and celebrated sports figures of the 20th century. (Supplied)
Greice Santo, wife of RJ Cipriani, is best known for her role as an actress in the show Jane the Virgin. (Supplied)
Locked and loaded with seven-figures in the war chest, the casinos roll out the red carpet. Just listening to Cipriani gush about the comp deals is intoxicating.
"I am not loyal to a casino unless they provide me with an incredible deal," he makes clear. "They will send $65 million private Gulfstream jets to come and pick me and my guests up and fly me to the casino."
Pretty much everything will be free. Michelin-starred food at celebrity restaurants, limitless bottles of the world’s finest alcohol, spa and beauty treatments, designer clothes from outlets in the hotel, VIP tickets to the best shows. Everything.
"Most of the time I travel as a lone wolf, or with my wife. I wasn’t the type to bring a whole slew of people in," Cipriani says.
"But at the beginning I would want to spoil everybody and I would bring a jet full of people and put everybody in penthouse suites. I’d sort out comped dinners, clubs and spa appointments for everybody. But it just didn't turn out for me good at the tables when I did that.
"It's not conducive to a pro gambler because you can't concentrate. You can't have any deviations and distractions, worrying about people eating and who wants to go to a show. It f--ks your head up if you bring a plane-load of people with you."
A den of sex, drugs and gambling, Las Vegas has always been regarded as the most hedonistic city on the planet, a modern day Sodom and Gomorrah.
Cipriani has gambled alongside Tiger Woods ("bit of a jerk"), Michael Jordan ("a cool guy"), Ben Affleck and Leonardo DiCaprio. Woods loved to bet big in Vegas, and was famously seduced by the dancers and high-class escorts who flock to the desert city, determined to make small fortunes of their own.
"The casinos will help high-rollers get the girls, the most beautiful girls in Vegas," Cipriani says.
"They have people in places and they can bring the girls into the hotel through secret entrances so nobody can see them. Fortunately, I never needed that."
Cipriani says before he got married there would sometimes be 20 girls frolicking in his private pool at the famous Hugh Hefner suite at The Palms hotel.
The pool, with its Playboy insignia embossed on the floor, is open-air and sits at the top of the hotel, with spectacular panoramic views stretching out across Vegas.
None of this comes for free, of course. Over the course of a decent session Cipriani says he could either "make a million-plus or blow a million-plus".
RJ Cipriani says it was common to rub shoulders with Tiger Woods, Ben Affleck and Michael Jordan in elite hotels, rooms and clubs in Las Vegas. (Getty)
The Hugh Hefner suite at The Palms, Las Vegas: 'Before I got married I used to have 20 girls frolicking in the High Hefner pool,' Cipriani says.
"As a gambler, one day you're on top of the world and the next you want to jump off a bridge or a high building. That's why there's no suites with open windows or doors in Vegas … I'm being dead serious."
High-rollers are given unique, pre-arranged discounts on their losses. If a gambler blows $500,000, for example, the casino might give them a 20 percent discount from that amount.
The other "incredible advantage" casinos give to their high rollers come in the form of free money to gamble, known as promo chips.
"It's not out of the ordinary to get $100,000 in [promo chips] just to walk in the door," Cipriani says.
"Sometimes I never have to touch my own cash and can win hundreds of thousands with their promo chips."
Blackjack is Cipriani’s game. He only ever plays in private rooms, where there is no one inside but him, a dealer and a supervisor.
Most Vegas casinos have a maximum blackjack bet of $75,000 per hand, spread across two or three spots.
This means Cipriani can sometimes end up with $250,000 - $300,000 on the table, if he is dealt cards that allow him to split or double-down on.
"It can be ridiculous, when you're betting a f--king Ferrari or a small house on a hand of cards."
Cipriani says he would sometimes "blow the mind of strangers" by letting them in on his comp deals.
"If you were lucky enough to run into me at Vegas, I would take you to the spa, get your hair done, your makeup done, full body massage, pedicure and manicure."
One time he forced The Paris Las Vegas casino to give a random woman and her wheelchair-bound elderly husband he'd met in the hotel lobby a penthouse suite next to him, just because he could.
The casino initially didn't want to allow the booking, but Cipriani threatened to pack his bags and walk.
"As a high roller you have that kind of power to tell everybody to go f--k themselves unless they do exactly what you say. I don't push it to the limit where I'm a prick or try to belittle people. But this is about me touching people's lives."
Cipriani recounts winning big one night and sending a bunch of casino limousines to be loaded up with pizzas for all the workers, "including housekeeping”.
The casino boss told Cipriani to stop, because it could be interpreted as bribing the dealers. So, the next night, Cipriani booked out one of the casino's restaurants so workers could come eat after their shift.
Cipriani's stories can sometimes sound so outrageous they border on the far-fetched. But here's the thing, he has the photos to back it up.
There he is, just like he says, singing on stage with music mogul David Foster, the producer for Madonna, Jennifer Lopez, Michael Bublé, Whitney Houston and countless others. There he is with comedian Andrew Dice Clay after hijacking the marquee sign outside the venue for a joke.
RJ Cipriani singing on stage in Las Vegas with music mogul David Foster. Casinos give high-rollers front row, centre stage seats to the biggest shows in town, Cipriani says. (Supplied)
RJ Cipriani as Robin Hood 702 on the cover of Seven, the Las Vegas casino bible (left); The marquee board advertising comedian Andrew Dice Clay that Cipriani hijacked and added his name for a joke. (Supplied)
The stories about Cipriani are out there and documented, from Vanity Fair through to the Las Vegas dailies, including his charitable work as Robin Hood 702.
Robin Hood 702 was an identity adopted by Cipriani where he would gamble for people in need and then donate his winnings to them.
"I like to do things that have never been done before, as far as treating people well," Cipriani explains.
"Because I'm this regular guy who became this high rolle