Comedian Ali Siddiq is bringing his Custom Fit Tour to Tallahassee on Saturday, Sept. 6, with a stop at the Donald L. Tucker Civic Center. Ahead of the event, Siddiq sat down with Josh Johnson, host of WFSU’s “the Warehouse” podcast, for an in-depth conversation on family, fashion and finding your own path.
And contrary to first appearances, Siddiq said his current tour’s name isn’t about his tailored suits. It’s about the people he’s chosen to keep close.
“It’s really about the people in your life,” Siddiq said. “In order to succeed in life, you have to have a great team, and you have to cultivate that team.” He said that sometimes means letting go of relationships that no longer fit, the same way a person outgrows old clothes.
“You have fitted your team for success, and you have fitted your life for success,” he said. “And some people don’t wish you the best.”
Building material meant to last
In his standups, Siddiq often weaves tales of family, friendships and situational ironies in a way that’s much closer to traditional oral storytelling than just back-to-back jokes. And Siddiq says that’s intentional. He avoids referencing presidents, news events or specific years in his specials so the material doesn’t become dated.
“I wanted to be something to where when my son’s son puts up, ‘Hey man, this is my grandfather’ — the date doesn’t matter, but the story does,” Siddiq said.
Reflecting on fatherhood
Much of the interview centered on “My Father,” Siddiq’s special about growing up largely without his own dad. Siddiq has said he is responsible because of his mother, but good because of his father’s absence — using it as a model for what not to repeat.
“The driving force to being a good father — a present father, a financial father, an emotionally connected father — [is] because those things my father was not,” Siddiq said. He recalled his father asking why he was angry about being left as a young child. “I cannot allow my children to ever feel that way about me,” Siddiq said.
“I’m the same person”
Johnson asked whether Siddiq’s comedy functions as therapy — for his audiences and for himself. Siddiq said he sees performing as a way of staying connected to the people watching him.
“We are connected through the thread of being human beings,” he said. “What I go through, what I feel, what you suffer, your triumphs and your falls — I’m the same person… I never want people to look at me, or me to look down on them.”
Conversations with incarcerated men
Siddiq, who has spoken publicly about serving time earlier in his life, talked about speaking with incarcerated men on “Ali Siddiq: From Inside” — work he said carries different weight coming from someone who has “worn those clothes, slept in that bunk.” Siddiq filmed inside a county jail with the goal of creating a message that could help break the cycle of incarceration.
During his visit with The Warehouse, Siddiq recounted an earlier story about a fellow inmate who was arrested for a robbery despite witness descriptions that didn’t match his appearance. He says that inmate came to see his imprisonment as connected less to that specific charge and more to a promise to God he made and broke after an earlier release.
“This is not a man’s crime that I’m in here for,” Siddiq recalled him saying. “This is a spiritual crime.”
Siddiq said the story changed how he thinks about accountability. “The main account that I’m concerned with is not my bank account,” he said. “What I’m concerned about is my spiritual bank account.”
Learning from elders
Siddiq said he relies on mentors older than himself when working through personal or professional challenges, including the late Anthony Colbert Sr.
“I don’t listen to respond. I listen to learn,” Siddiq said. He described Colbert’s method of calming him down with an unrelated story before offering advice. “You cannot beat experience,” Siddiq said. “You get somebody who builds tables, and you get somebody who can read, and you give them an IKEA table and directions — and see who finishes first.”
On legacy
Earlier this year, Siddiq received an NAACP Image Award for the special “My Two Sons.” It marked the first time an independently produced and released YouTube special won a major award. Asked what he wants his legacy to be, Siddiq said he wants his children to pursue whatever makes them happy, with his support as a safety net rather than a set of expectations.
He pointed to his oldest daughter, who told him she wanted to be a chef, went through culinary school and now owns a restaurant.
“I gave her all the rope — not to hang myself, all the rope for safety,” Siddiq said. “Go out as far as you can go and just know it’s tied around my waist… Live free.”
He said the same applies to his younger brother, who installs TVs and does handywork for a living. “I don’t care if you’re laying carpets — be the best, efficient carpet layer,” Siddiq said. “If you’re happy doing it, you never measure yourself by other people’s standards.”
Johnson closed the interview by describing Siddiq’s work using what he called the “3 T’s”: therapy, testimony and talent.
Watch the full interview with Josh Johnson on this episode of “The Warehouse.”
