Hometown comic Pat McGann headlines the Chicago Theatre this weekend — he made a bet on himself and won

The stand-up comic Pat McGann was in Las Vegas over the weekend. It was not the first time he has visited Las Vegas. He has been there many times over the years, recently making people laugh and, many years ago, when he was in a vastly different profession, selling paper and packaging.

“That was in 2007 and I was good at my job,” he says.

Still, Vegas was made for gamblers and that was when he decided to roll the dice, quitting the packaging business to pursue a career in the precarious and often heartbreaking world of comedy.

He was 31 and he was a winner. He reaches a notable milestone Saturday when he headlines two shows at the Chicago Theatre, which has more than 3,500 seats, a much, much bigger venue than the 100-seat Zanies where I first saw him.

“Oh, yes, I do remember,” he said. “When we recall those days, the Chicago Theatre can seem unattainable, certainly intimidating. But I have been on that stage before as an opening act but I have to say I never imagined any of this.”

He was in Vegas this last weekend to give a private corporate performance. He came there with his parents and three children (wife Sara remained in Chicago). This family jaunt was fitting, for it is family, the weirdness and wonder, chores and delights of it all, that has formed the firm foundation of McGann’s comedy.

It took him a while to realize that, saying, “I think when I was first on stage I was a bit too removed from my material. Once I started to get personal, and that was a risk, it became quickly and increasingly genuine, I think I became better at connecting with my audiences.”

There is indeed a palpable authenticity to McGann’s material. He works “clean” and is a fine and polished storyteller. He’s a keen observer with an engaging stage persona, still boyish even as his hair gets peppered with gray. Though he now varies his material to suit geographical settings and venues (you don’t joke about Western Avenue taverns when performing in Seattle), the marquee of the Chicago Theatre might as well be emblazoned with “Local Boy Makes Good.” McGann is as local as it gets — child of the Morgan Park-Beverly neighborhoods (St. Cajetan parish) and 1994 graduate of Marist High School. He is the youngest of three children, his older sisters are CPS teachers.

“I’ve always been trying to make people laugh,” he said. “Seemed like all my friends were funny when I was younger. I could write too and started going to open mics night at clubs and watching people perform. Some were funny, some were not, and that gave me some confidence. I had never been on a stage but figured I could put together three to five minutes.”

His parents were also supportive. “They took me to see Seinfeld when I was young and whenever they went to another city, like New York, they would come back home and talk about the club they went to, the comics they saw. That helped give me the get up on stage, their support and that of my wife and kids.”

He first performed at Zanies in 2008 and caught the eye of the club’s executive director Bert Haas, who had seen many thousands of comics since starting work as a server at Zanies in 1980. It didn’t take long for Haas to offer McGann the steady job of house MC.

“From the first time I met Pat I knew he would be successful,” says the now-retired Haas. “Not just because he is so incredibly funny but also because he has a business mind, sometimes hard to find in an artist, and he is so well-liked by everyone. Observing Pat as house MC at Zanies, I was always amazed by his incredible quickness when working with a crowd. I’d rank him the fourth-best comic in my experience, behind only Jay Leno, Jimmy Brogan and Paula Poundstone.”

McGann benefited not only from the almost constant work and interaction with audiences but from observing hundreds of comics (from stars to duds) and soaking up whatever knowledge, advice, connections or warnings they were willing to share. He was soon working at other clubs, making frequent radio and television appearances, national and local, notably hosting “Chicago Stand-Up Project,” a fascinating WTTW-Ch. 11 program that featured McGann coaching such “regular” folks as Father Tom Hurley of Old St. Patrick’s Church into performing as stand-ups.

And it was at Zanies that McGann first saw Sebastian Maniscalco, the now immensely popular, arena-filling Arlington Heights native who has, McGann says, “jet-fueled my career.”

“I would say that we slowly connected,” says McGann. “He was so solid on stage and I learned so much every time I watched him. He is such a workhorse and we did have many things in common … local guys, father of young kids.”

They became friends and Maniscalco asked McGann to be his opening act at a Harris Theater show taped for a Showtime special. They really bonded some years later, when they began performing together at national theaters and arenas. The pair played four sold-out shows at New York’s Madison Square Garden.

Maniscalco produced “Sebastian Maniscalco Presents Pat McGann: When’s Mom Gonna Be Home?” which was filmed at the Vic Theatre in 2019.

“Pat had been flying under the radar for so long, I wanted to give him a platform, a coming out party,” said Maniscalco at the time. He was well aware of the effect such a show could have. He vaulted to stardom after actor Vince Vaughn featured him in 2006′s “Wild West Comedy Show: 30 Days & 30 Nights.”

“When’s Mom Gonna Be Home?” premiered in 2020 and then came the pandemic, obliterating live performances and forcing performers onto new creative roads. McGann’s innovative way was captured by my colleague Chris Borrelli.

Now, McGann’s schedule is filling up with performances around the country, the future looking bright, though he is shadowed by the fact that his family life is undergoing changes. Talking about the activities and inevitable antics of 3-year-old or 4-year-old children is vastly different from offering crowds details of soon-to-be teenagers.

“For so long the kids didn’t have any idea about what I did but they are into it now,” he says of 11-year-old Josephine, 9-year-old Elliot and 8-year-old Luke. “They have seen me perform. They know what I do. My daughter has started doing plays. She is so comfortable on stage.”

In Vegas, he did not gamble, saying “I rarely gamble, I get enough of a thrill from stand-up and driving on the Dan Ryan.”

7 p.m. and 10 p.m. at the Chicago Theatre, 175 N. State St.; www.patmcganncomedy.com

rkogan@chicagotribune.com