Musician Michael McDermott returns to perform at the jail where he was held after drug bust

The first time singer-songwriter Michael McDermott walked through the gates of Cook County Jail was Nov. 23, 2002, after being arrested at the House of Blues for cocaine possession.

He returned this week in a different capacity: musician.

It was his third visit to 26th and California, his second time as a performer.

Up to his arrest, McDermott, who grew up in Orland Park, lived a high-risk life balancing a successful musical career with a raging drug and alcohol addiction. He was recording for major labels, appearing on MTV and performing on late night television while smoking crack cocaine and experiencing close calls with law enforcement. He would get sober 12 years later.

Despite living a different life today that includes being a husband and parent, McDermott said the prospect of returning to Cook County Jail to play music, which he did for the first time last year, was “traumatic.”

“The place created monsters in my memory,” he said. “It was a culmination of a lot of madness and a lot of bad behavior in my life. Today it’s more about shame about the way I lived my life that I still carry.”

On Monday, McDermott relayed those feelings to an audience of 100 incarcerated men who did not know him or his music. He walked onstage with a guitar and introduced himself. The room was bubbling with energy — the men talking, laughing among themselves. Then, when McDermott told them he was once a detainee himself — “I never figured I would come back,” he said — the room fell silent.

What followed was a series of original songs — “Parolee,” “Last Chance Lounge,” “Butterfly,” and others — that documented the drug-fueled chaos of his early life. Switching between piano and guitar, McDermott preceded each song with a personal story — freebasing with a cabdriver in Denver or wandering carless west of Chicago after spending all his money on drugs — that kept the room transfixed. He also revealed another heartbreak — that he wasn’t the only person in his family to spend time at the jail. His father was booked there on a gun possession charge in 1995, he said.

Some men leaned forward to listen more closely. Many clapped along; others stood to applaud once he was finished. He performed three encores. Two dozen men then gathered at the front with McDermott for a group picture.

“He just got me through the day,” one man said afterward. Another said, “He’s real life. He’s not sugarcoating it. He’s telling it like it is.” (Both men declined to provide their names.)

More than 40 artists, from the Wailers to Michael Franti to Shemekia Copeland, have performed at the famed correctional center over the last nine years. The site is also where blues guitar great B.B. King recorded “Live at Cook County Jail,” one of his most legendary records, in 1970.

Cook County Sheriff Tom Dart said the McDermott concert was part of an effort at the jail to elevate the men with hope, especially those suffering from longtime drug and alcohol addiction. Although he is a longtime fan of McDermott's music, Dart said he only met McDermott last year, and was impressed by how much of a connection his music made with the audience.

“How could it not? He talks about his family and his struggles,” Dart said. “His stuff is so real. It has something that connects with all of us.”

Beyond music, the rehabilitative programming at Cook County Jail under Dart includes a culinary program, an urban farm, chess instruction and art classes, as well as programming for mental health workshops and addiction recovery. Afterward, Dart spoke to the audience to push them to participate in any or all of what is available to them in an effort to move their lives in a different direction once they returned home to their families.

“We aren’t destined to do anything. We can do whatever we want,” he told the men. “You can change your own role in life.”

During the hourlong performance, the music echoed the sentiment.

“Sometimes you need the darkness in order to see the light,” McDermott sang.

“A lot of these people, they’re the forgotten in a lot of ways. So I want them to know that whatever they’re going through, they’re not alone,” he said before the show. “Whether you’re working in a high-rise or you’re a street vendor, we all have a shared experience.”