At long last, HBO is dropping Bookie Season 2, starring legendary stand-up comic Sebastian Maniscalco and Omar J. Dorsey.

Bookie, for those unfamiliar, follows a sports bookie, Danny (Maniscalco), and his enforcer, Ray (Dorsey). They are struggling to keep up as the sports betting world evolves. The second season picks up right where the first left off.

For Maniscalco and Dorsey, they have seen this happen in their respective industries. Maniscalco, who earned his stripes as a stand-up comic, is aware that the business is changing. Last time we spoke, he acknowledged that social media is changing how comics get famous. However, they still need to get their reps in front of an actual audience.

“I think stand-up comedy has skyrocketed over the last 10 to 12 years; live entertainment seems to be extremely popular,” Maniscalco said. “You've got people filling out arenas and theaters [with] stand-up comedy — theaters are like the new comedy club.”

Sebastian Maniscalco at the Oscars in 2020.
Dan MacMedan-USA TODAY.

While there have been lots of positives, what Maniscalco “fears” is comics taking shortcuts. For himself, there was no social media when he was coming up in the '90s. So, he had to take gigs in bowling alleys and restaurants to hone his craft.

“My fear is with the invention of social media and these quote-unquote comedians that are doing funny online videos, you are not going to see a lot of people going out, putting in the type of work that they need to put in to be a seasoned stand-up comedian.

Ultimately, he hopes people don't go “so towards” social media that they lose sight of the industry's roots and that coming-up acts don't go the social media route.

How social media affects acting

Speaking of social media, Dorsey voiced similar concerns with acting. Dorsey acknowledges the positives of the “expansion” of TV, with several streaming services currently thriving.

However, there is the social media aspect of his job. Sometimes, actors have to use their platforms to promote current projects. This is something that Dorsey claims to “hate,” as he just wants “to do my work and go home and kick it with my friends, wife, and kids.”

“It's like a whole nother job,” Dorsey said of using social media. “With technology, you have to be able to do all of these different things.”

Bookie takes place in California. In the show, sports betting is just being legalized. Dorsey has sympathy for the bookies in the state, as they are at risk of becoming “dinosaurs.”

“Luckily, in California, online gambling is still illegal, so people still have to go to their bookies. Their job is pretty safe,” explained Dorsey. “But it's only a matter of time before FanDuel and DraftKings merge over and become a part of California, so they might become dinosaurs.”

The glimmer of hope for Dorsey is that people are still yearning for a “human connection.” In turn, he believes bookies will still be around so people can place bets in person, “not just doing it on their cell phone.”

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Bookie stars Sebastian Maniscalco and Omar J. Dorsey's worst bets

Omar Dorsey and Sebastian Maniscalco.
A still from Bookie courtesy of Max.

Everyone makes bets. As a kid, it is second nature to bet your siblings and friends on anything and everything, from how high you could climb in a tree to whether or not the shy friend could get a girl's number.

Years ago, Dorsey bet a kid his Tecmo Super Bowl game that he was faster than him. If Dorsey won, he would have received three G.I. Joe figures.

Unfortunately, Dorsey got smoked: “He dusted me. I got in really bad trouble with my mom — she whooped me when I got home.”

Luckily, Maniscalco doesn't recall any bad betting stories with embarrassing consequences. However, he did go to Las Vegas years ago and had to pick up “so many shifts” at his job at the Four Seasons Hotel to cover his losses after losing money at the blackjack table at Treasure Island.

He may not have had to shave his head or adjust his mortgage, but it still had consequences on his career: “It took me away from comedy for a little bit,” he confessed.

It all worked out, and Sebastian Maniscalco is now starring in Bookie Season 2. As he and Dorsey had to learn, some bets pay off, others don't.

Bookie Season 2 is airing on Max.