Any Sopranos and poker fan would have been envious of Robert Iler’s seat at the table. Actors and crew from the show crowded around a table in James Gandolfini’s Los Angeles hotel room. Players checked their cards and bet and bluffed, tossing coins in the middle of the pot.
The small-stakes poker game had broken out the night before the Emmys and Iler was right in the middle of it. He played Tony Soprano’s son AJ on the show and had already been acting for more than a decade.
Iler had also been playing poker since he was young, which fostered a love of the game. His grandmother taught him to play and not only was that night a great experience, he walked away a winner.
“We just had a ton of change and everyone was just playing for fun,” he says. “I remember leaving the room with a hotel glass from the room filled to the top with quarters.”
The Sopranos may have ended its run in 2007, but poker would remain a big part of Iler’s life.
A gambling life and playing online poker
Many players have a fond memory of a family member breaking out a deck of cards for some penny-ante poker. For Iler, those games involved his grandmother teaching him numerous card games as a youngster.
By age 18, Iler began playing poker with friends even more and was soon heading to New York’s underground poker rooms. Because of those early games, Iler always felt comfortable playing and had a knack for cards.
“I just realized that I always thought poker was something that everybody knew – the rules, the structure, and how it’s done,” he says. “But I’d notice all my friends couldn’t remember what beat what or they didn’t understand.”
Poker became a regular part of life – both live and online. On trips to the the Borgata, Iler enjoyed the side action during World Poker Tour stops. He describes the cash games as a “dream.”
On The Sopranos, gambling was a regular part of life for Tony and the gang – many times the unsavory aspects. Members of the cast were also known to bet and throw some dice on occasion. Iler remembers a few trips with cast members that involved some gambling.
“There were times where we would go to casinos to do appearances and they would give everybody a hotel room,” he says. “We were always playing Blackjack and I would go play poker. Once they went to sleep, I’d play poker for 12 hours.”
Life after the Sopranos – heading to Vegas
When The Sopranos finished its sixth and final season in 2007, Iler craved leaving the acting grind for a while. While other cast members jumped back into work, he’d been acting for years and needed a change.
“Give me six months,” he told his manager at the time. “I just want to hang with my friends and do nothing.”
That turned into a decade of basically avoiding acting and playing live and online poker. When Black Friday hit on April 15, 2011, Las Vegas seemed like a nice spot to land. He planned a two-week trip to play in the World Series of Poker Main Event.
The trip produced his first WSOP score, cashing in 275th for $40,654. After that, his two-week Vegas jaunt turned into two years.
“I literally took that check and said, “I’m going to put this in an account and pay my rent with it and just pretend like I never had it,’” he says. “A year and a half later I was still there and I was just heavy into drugs and partying.”
At 25, Iler’s Vegas life mostly consisted of gambling and partying. His substance issues have been well-documented and he knew some growing up was needed. That turned out to be the right decision and he’s been sober since 2013.
“I remember thinking that I had to get out of there because I started losing what reality is,” he says. “I’d be in a strip club like on Wednesday afternoon at 1 pm, just the dumbest stuff. Then my friends came to visit me and were like, ‘Yeah you need to get out of here.’”
Moving on, venturing into podcasting
Recently, Iler jumped into a new venture that involved his skills as a communicator and actor. In the process, he reconnected with an old friend from The Sopranos – Jamie-Lynn Sigler, who played his sister Meadow.
The two got reacquainted during a 20th anniversary event for the show. Afterward, the two jumped in their pajamas and spent the night reminiscing.
“I’m sick of Vegas,” he told her. “I need to get out of there. I need more stability.”
An idea for a podcast began taking shape. Iler and Sigler teamed up with YouTube comedian Kassem G. for the Pajama Pants podcast. The show launched just before the Coronavirus pandemic began after Iler moved to Los Angeles.
Plans called for living in L.A. for at least a year, podcasting and mixing in some occasional poker. The pandemic has thrown a wrench into those plans, but the podcast has been going well, he says.
Pajama Pants now has regular sponsors and has attracted a nice following. The show focuses on various topics with poker even occasionally thrown in.
Maybe surprisingly to fans, The Sopranos is rarely brought up.
“It’s fun – we’ve had some great guests, we have sponsors now, and are doing commercials every episode,” he says. “We don’t really talk about Sopranos because I never watched it and people are so hardcore about Sopranos and they know so much, why would two people who don’t know anything about it talk about it?
“Sometimes we may talk about things that happened on set or memories that we have, but 90 percent of our podcast has nothing to do with Sopranos.”
Hitting it ‘big’ at Global Poker
During the site’s GOAT series this summer, Iler received a Global promotional email touting the festival. He thought he might have a few bucks left online and checked his account.
With 40 Sweeps Coins left (the site’s virtual currency allowing players to exchange for cash prizes), he jumped in a Super Bounty with 5,000 Sweeps Coins guaranteed.
The event attracted 752 entries and before he knew it, Iler was at the final table. The thrill of winning would be nice, but a sharp-looking Global trophy also drew his interest.
“My friend had to tell me, ‘You know you get a trophy right?’” he recalls. “When the trophy came in the mail I was shocked.”
Snagging that trophy, and the 720 Sweeps Coins plus bounties that went with it, wouldn’t be easy. Despite being chip leader in the late stages, a big late hit left him with about three big blinds. He rallied, however, finishing off his opponents and earning that GOAT trophy.
The topic was even brought up on Pajama Pants and Iler showed off his shiny new trophy. The show then ran a Global freeroll tournament for listeners, which drew more than 300 players.
When the pandemic is over, Iler definitely plans on heading back to the live poker tables. He hopes to enter some major events, perhaps the WSOP or WPT.
When it comes to poker, one thing comes to mind for Iler – freedom. There are no bosses, directors, or anyone else telling him when to be on set, what to say, and how to act. He can simply sit and battle it out on his own terms.
“You go play poker and there are no rules,” he says. “You can come whenever you want, sit wherever you want, play whatever game you want, and leave whenever you want. Since I’d been acting since I was six years old, I think that’s what was so attractive to me about poker.”
* All seasons of The Sopranos are currently available for streaming on HBO Max.
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