If you were to ask Ali Siddiq, 27 years ago, where he thought he’d be by the time he eclipsed 50, chances are his answer would’ve been much different than his current reality. But with an ever-evolving sense of self and an unwavering yearn to grow, the critically-acclaimed comedian has decades worth of perspective and experience behind him that has forged him into the person he is today – and he wants nothing more than to continue sharing more of that with the masses.
So that’s what he’s planning to do when he makes his way to Boston’s Shubert Theatre tonight (May 30) as part of his In The Shadows tour. Following the success of a flurry of stand-up special including his multi-part Domino Effect series in 2024, as well as his most recent release in My Two Sons, Siddiq has offered his audience an unfiltered, and often times poignant and deeply personal look into the happenings of his life before and after fatherhood, and he looks to continue on that journey as he details his path to the comedy stage in his latest slate of material. Meshing elements of storytelling and energetic, physical comedy, Siddiq has become of the brightest stars in the game, and while he certainly has room to gloat about his accomplishments, he’s keeping things humble and honest as he carries on with sharing perspective, and hopefully helping others along the way.
We had a chance to get the Houston native on the phone recently, where we covered the new show, the evolution of his creative approach, the joy of being a lifeline and helping hand for others, his appreciation for Boston-born comedy and hip-hop, and so much more. Check it out.
Jason Greenough: Just getting started, thanks for connecting. I’m looking forward to seeing you roll through the city again, and with that, you’re bringing your In The Shadows tour to the Shubert Theatre. Starting there, what are your thoughts on coming back to Boston with this new show?
Ali Siddiq: I’m excited for people to see my new work, and I’m also excited that I’m going to get an opportunity to do it uninterrupted. That’s been the biggest thing for the last four or five weeks, where we’ve been doing a lot of things, and so now we’re starting to record the set and sending it out, so for the first three months of the tour, I wouldn’t do any of the material for In The Shadows, but now I’m finally able to work the material of this show, and I’m very excited about it.
As you should be, because for anyone familiar with your work, they know just how elite your jokewriting and storytelling abilities are, and your ability to intertwine the two is a whole other conversation. But what can people expect from this show, especially after they’ve seen your latest specials in My Two Sons and the Domino Effect series? Do you look to add any new elements to your approach on this one?
I must say, with Domino Effect, there were a lot of heavy stories, then I lightened the load with My Two Sons, which had more of a physical and energetic storytelling approach. With In The Shadows, it’s a combination of those two shows, as I walk through how I got to this point in my life. In interviews, and even by other comics, I’m asked all the time about how I got here, so this show is walking through how I got started in stand-up and telling stories, and where me being jovial actually came from. It’s therapeutic for me, and it’s a work piece that looks at how people might work in the shadows of certain vices or things they might be embarrassed about, and I worked through it, so I’m also talking about how to deal with those elements.
Having been formally incarcerated, I never wanted to be put in a position where anyone knew anything about me,so I would avoid talking about myself in detail. But this time, I’m talking about how you can break away from those components of being ashamed of certain things you’ve been through in your life.
That feels like a perfect combination of things, or the light and dark of Domino Effect and My Two Sons, and I’m excited to see it. Was it a natural progression to tell thai part of the story next?
After being asked so many times about how I got here, the elements just came together to create the blueprint and storyline for how I accomplished what I’ve accomplished, and give people an angle of mental fortitude with my stand-up. That’s a main component of me being vulnerable in certain aspects of having a true story to tell, and giving people some guidance based on my particular life, obstacles, and what I’ve overcome. I’d like to think of this show as also something motivational, where it has a lot of the components of a therapeutic journey in trying to be better.
Was that something you realized before telling the story, or did that throughline present itself while you were still piecing things together?
When I started formulating it, I went into it with the thought of where I wanted to start with it, and map out the first forty-five minutes as a way to progress to the last 15 or 20 minutes, sort of like an advanced Domino Effect, where you’re almost getting two parts in one.
Do you still think it’s effective if we have an In The Shadows series like you did with Domino Effect? Or was that approach something that was special for that part of your story?
Ah, you beat me to it. Spoiling the element of surprise of me telling you, In the Shadows will be three parts. That’s just a good way for me to keep it continuously fresh, and to give people a different stroke on stand-up, in general, really. You don’t have to cram everything into one hour. Doing it in parts, you give people a series, and being a big fan of well thought out series myself, like John Wick, or The Equalizer, or The Fast and The Furious, even though I don’t go past five. Placing it in that way, it allows the story to continue in a way where people can digest it easier, and have a bit more understanding of it.
I love that, and I can’t give you enough kudos for what you’re doing with the delivery of these stories. It’s continuing to redefine the idea of comedy specials and albums, for sure.
Well, thank you. While I want to tell the story of how I emerged out of the shadows, I also want to shine a light on the people who helped me along the way, because I definitely want to stress how we need community, and how it’s not just me doing this. You need a community effort and people investing in you as you go along, like I found, and some people were helpful and others were, for lack of a better term, very mean, but I needed that too, if that makes sense. I look back on it now, how my grandfather was a very stern man, but that sternness gave me structure, as opposed to my grandmother, who was very light about life, and that made me jovial and helped me understand how jovial I was. Once I realized that I can enjoy a journey even though it has some bumps in the road because that’s a part of the learning, as well, it brought a new perspective.
It gives food to me stand-up, instead of it being all laughs. That comes from a comedian named Billy D. Washington, who told me that when I’m on stage and not being funny, I need to be interesting. So I adopted that ideology, and it has worked. Between Domino Effect and My Two Sons, I was going through some things early in my life, but how my sons turned out is my lane. I was a certain person at one point in my life, and now I’m this person, so my sons are different people, and sometimes, parents get caught up in seeing how different their kids are, but where were you in the process of that? You haven’t always been the fifty year-old you. My mom always asks me if she was a good mom, and I’m like “I’ve been with you since you were twenty. Now you’re seventy-two. You developed into a great mom, you got there. You thought you were a finished product at 20?
I’ve had those conversations with my parents too. At the end of it, it really comes down to the fact that you don’t have to enjoy the ride all the time, but you have to at least appreciate it for what it is. I’ve always appreciated that deep perspective in your comedy that is focused on growing, and learning, and figuring it out as you go.
That’s what comedy has been for me, because I remember being twenty-five, never thinking I would be doing one thing for 27 years. Even with other jobs in the middle of it, the focus was still achieving the goal of being a successful comedian. So that has allowed me to enjoy this, being able to be in this space, and being so comfortable in my skin that I can share almost anything and be totally fine with it. I don’t have these woes and hang-ups that other people might have, so I can hopefully help people with working through that.
Taking a look back at twenty-seven years, it’s an impressive number to stand by. So much has gone on in that time, and the ways of so many different things in our culture have evolved over that time. With the past twenty-seven years in mind, what has been the most fulfilling part of your career, as it stands now?
If I can honestly say, producing another comic’s special. I produced Marcus D. Wiley’s special Marriage Is Major Surgery, and I think it is the best thing in stand-up that I’ve ever done, to be able to facilitate another comic’s voice and work, with no ego. It’s not my project, it was his project, and I was able to offer a helping hand, but I take the utmost pride in saying I was able to help. Just like with my daughter becoming a chef. It’s her accolade, not mine, but I always have wanted to be a helping hand in life and in comedy, not just a comedian. I haven’t been in the mindset of being selfish in quite some time. I just never saw the benefit of being the only one.
Nothing but respect for that, Ali. Thank you for your time. I have one last question before we go, though. What are you looking forward to most about this return to Boston in this new chapter of your career, even aside from the show?
I’m really looking forward to bringing the new show to Boston, and showing the people the dynamics of putting together a completely different show. I’m not doing material from any of my past specials, or the one coming up on Father’s Day. It’s a whole new hour, and that’ll show the diversity in how I think and how my mind operates. I’m also excited to see some new faces, and hopefully some old faces. I used to come to Boston comedy clubs, and I’ve had some experiences in Boston that were different, and I’m just excited to be back in the city.
It’s a city that a lot of people that I respect come from. I have the utmost respect for people like Patrice O’Neal and Bill Burr, and Ed O.G. & Da Bulldogs. They were the first rap group out of Boston, and how I learned about Roxbury. And of course, being in the home of New Edition, who are my Temptations, and people like Bill Russell, there’s just a lot of history in Boston, and I love being in that.
ALI SIDDIQ: IN THE SHADOWS :: Friday, May 30 at Shubert Theatre, 265 Tremont St. in Boston, MA :: 7 p.m., tickets start at $34.50 :: Event info and tickets