His sets are intimate accounts of his life. Each stand-up special is expertly tied together under one theme, as if he’s giving the audience his memoir in real-time: each set marks a new and exciting chapter.
What’s interesting about Siddiq’s career is that he was able to amass his fan base organically on YouTube as an independent comic. He was even deemed by Vulture as “stand-up comedy’s most prolific storyteller,” in 2024.
Many people may have been introduced to Ali from his 2015 appearance on Comedy Central’s This Is Not Happening, where he opens up about serving a six-year prison sentence. As quotable as that special is, I can’t quote it on public radio without violating FCC policy, so you’ll just have to look it up.
He may be best known for his work after 2015, but Ali has numerous credits dating back nearly three decades. It’s remarkable that someone in the game so long was able to change his approach with the turn of technology. So much so, that other comedians are beginning to follow suit.
In 2022, he released his groundbreaking special The Domino Effect Part 1, which has garnered over 19 million views. His most recent YouTube special, Mondays, has reached over five million views.
Now, Ali’s back on the road again with his national Custom Fit tour, which he’ll be bringing to The Wilson Center at Cape Fear Community College on Saturday, May 2.
Here’s a clip from his YouTube special Mondays, just to give you a hint of his comedic styling:
“You know how they say easy, like Sunday morning. Lionel Richard said that song. Marcus says that all the time. He say it's easy, like Sunday morning. And I get that, but Monday… Monday is hard for some strange reason.”
“I don't care if you unemployed, if you employed, or you own your own business, whatever you're doing Monday is hard. I'm going to tell y'all four stories, all of them started on Monday.”
That still makes me crack up, even though I’ve heard that joke a dozen times.
That’s how I wrote my request to interview him, you know? I wrote: “It’s not every day you come across a comedian who makes you laugh the 15th time you hear their joke, as if it were the first. But Ali Siddiq is not your everyday comedian, is he?”
And that couldn’t be more clear after having the opportunity to speak with him one-on-one.
And just a note, that this interview took place over zoom, so some parts may be choppy due to connection issues, but a transcript of our conversation will be included on WHQR.org.
Here’s my conversation with Ali Siddiq not presented as the man on stage I thought I knew, but as the human I had the pleasure to get to know in our interview.
The Comedian…
Aaleah McConnell: With you being an independent comic, and you've managed to amass these millions of views, and you've gotten this award, which is the first ever of its kind to be awarded. How does it feel to know that you've carved your own path without having the backing from like a big network?
Ali Siddiq: I've been doing stand up for 28 years. So the first, the first major success was being on XM Radio, when that, when that first jumped off, you know, I released multiple albums, starting in 2009 but I think the mass majority of comics are independents.” You know, that's not assigned to labels or not agencies or management companies. They may not have had, they may not have not had national exposure, but it is a lot of independent conversations, you know.
But within that, some of them are looking for deals. Me, I have already had deals and decided that they wasn't the best route for me. So my independency started, then it stopped, and I went back to being independent. I had a special on Comedy Central. I've had multiple shows on Comedy Central. I'm assigned to deal with Comedy Central, and it just didn't fit me. And even if I was on HBO or Netflix, it still wouldn't serve me well because of the amount of specials that I would want to put out.
It's kind of like the the whispers or Earth Wind and Fire. People like, Earth Wind and Fire still torn. They like, yeah, it's, it's like they've been doing it for a long time. You just now finding out.
I think that a lot of people think that if you're not on social media, then your career is dead. But those of us who started before social media, what you think we were doing before that? You know, we, you know, years and years and years of being on the ring, being in places and performing and going to cities and doing comedy shows and doing comedy clubs and selling out places, long before social media even existed.
AM: You've been doing this, but you know, everything kind of ramped up, and I haven't seen a slow down or anything get in your way since then. So how do you what are you most proud of so far in your career?
AS: What I'm most proud of is keeping my word to myself. You know, I said when I was in a different situation that I was going to do this, and it didn't matter the the level it was like I want to do, stand up, not knowing how it worked because 94 when I thought of it, I didn't know how it worked. I didn't know what you supposed to do. I didn't know step one. All I knew is that I had the idea that I that's what I want to do. So getting out, and then 97 I get out, October, I'm on stage in December, you know, 97 September of 99 I'm on comic view. So within 18 months of me getting out, I'm on TV. “But that wasn't even the goal. The goal was just to become a comedian, not even knowing that this was something that could take care of me and my family.
AM: And I'm curious, when you do these interviews, what kind of questions do you wish that you were asked more often that you don't really get a chance to answer?
AS: Process. Process of comedy and thought and thought patterns. You know, people are interested, and I understand everybody's interested in what they're interested in, but some of my best interviews have been about the process and the journey of stand up, from being a stand up, you know, like that stuff. How does how this becomes passion when you don't know the the destiny, when you don't know how to even do do most people don't know that comedy at the time that I started, I didn't know anything about how to even start. I just know I wanted to start, but this is a, this is a labor from scratch.
So, with, with a road like that. It's a it's an untapped road that you have to mow down the trees, and you have to make the road, and then you have to build a house, and you know, it start like starting the community. You have to find the lanes that you are supposed to be in, and then you have to grow, you know, because kind of comedy is about growth.
But the development of comedy I'm really never asked about in in most interviews.
They kind of say, they kind of say those questions for who they feel like are The upper echelon comedians or somebody who's going to give some type of fluff answer and not really go into detail about it. So that's, that's, that's something it depends on who I'm being interviewed by, if they see the brilliance in the mind versus the sensationalism of certain things.
AM: Well, I definitely view, view you as one of the upper echelon comedians, you know, in my opinion.And would you like to kind of speak to the process?
AS: The process for any comic is depending on the road that they want to travel.
You know, I'm offended by certain things, like when they say that Bill Clinton was the first black president, yeah, but It was based upon him cheating on his wife and smoking weed and playing a saxophone. That's what, that's what makes you Black. That's the type of irresponsibility in a, in a in a person's words, that the masses will gravitate towards. But that's not my process.
So it's so many things in comedy that people can I don't even think people value comics as much as they they they even say, because what we do, what we do, is medicine. You know, what some of us do is medicine for people.
Before I walked into this interview, a lady stopped me and said that I got her through some, some very dark times, you know, in my life, that's because I'm, I'm talking about dark times in my life and how I and how I transcended through it, and what I leaned on, that's the that's the process. This is the first four or five specials. Is me unloading that baggage. And people like, Well, how did you how did you get here? Well, that's based upon me cleaning up the damage that I did to the community. And I've always say, I'd always say that, man, I never, I never get to another height until I pay back the universe for the damage that I did. But my thoughtfulness and my thought, my thought pattern, is different for most people. None of this, none of this stuff is is due to me. Any good that I have is from the Creator. Any bad that I do is from me.
The Storyteller…
AM: I do want to talk about the fact that you're an amazing storyteller. You were crowned stand up comedy's most prolific storyteller by vulture. As a matter of fact, who would you say is the most influential storyteller in your life?
AS: Oh, the various people in my family, my my mom, my uncle, my grandmother, it's not, it's not another comedian.
That's how I learned everything in my life through a story.
You know, I grew up listening to the whole when I had to go to school, I had to walk 35 miles in the snow. He said, That's everybody's life that I know it was saying, and it came from somebody in their family, and most of the time was in entertainment.
People think that it's another comic that influenced you. The funniest people that I know are people in my family. It's like my Uncle Mac and he's just telling, he just telling a regular story.
AM: On your special called Mondays, you did a little bit of that, where you kind of rifting with the crowd. Do you feel like that kind of comes naturally to you, or do you think that's a skill that you just develop as you get comfortable over time?
AS: I've been doing it for 28 years. I started off as hosting, so I'm just comfortable with an audience, because I don't write, I write the I don't write jokes, so I just have the stories so I don't have to, I don't really have to write a joke. I haven't wrote a joke in probably eight years. So when I do, when I do, when I'm doing the special is just me remembering what happened. There's not a lot of writing in the aspect of how I used to be when I was telling jokes or when I was writing from other spaces, such as politics and, you know, current events. So if people notice all these stories are just about me, and like with normal people, they don't have to write their story. They just have to remember it.
AM: How has you know being incarcerated and you know going through the prison system shaped how you've navigated your career in comedy. [36:19] Not necessarily you know, you talking about it in your stand up or anything like that. But how did that experience, you know, get you prepared for this?
AS: That's what I tried to explain a lot to people, that people try to paint me in this corner of being some incarcerated guy, that my my life lessons came from being incarcerated. My life lessons came from my family. My perseverance came from my family. My uplifting came from my family. My nation came from my family. Those things were just placed in the wrong atmosphere, being determined to achieve something that wasn't really who I really was, that a human being overall. So reverting back to my true self is really what shaped my my career.
AM: It's just, you know, something interesting that you don't shy away from. And I do appreciate that about you. As a matter of fact, when you did your 2018 from inside a conversation with inmates, I wanted to ask you, why was it important for you to go back to that setting and talk to people who are in currently inmates?
AS: Because those people understand that incarceration is not they, is not they life that's something that happened to you based upon mistakes. But this is not actually who you are and letting them know that people paint you into some incarcerated prison corner because you don't have to, you don't have to be that. And I explained, nobody even knew I was incarcerated until 2015 and they try to make that my whole, my whole career, even even now, Domino Effect wasn’t about being incarcerated. The first one wasn't about being incarcerated. Nor was the second. It was about becoming that person who was on the way to incarceration.
I know that I'm on that right path, because I didn't win, I didn't award for any prison special I want to for being a father With my two, my two sons. Then I run, I won award for, you know, being being vulnerable as an individual, that, hey, it's some things that I know and some things that I don't know, and I I'm not shying away from things that I don't know, because those are the things that I that I strengthen because I don't know, you know, and Mondays and Father's Day, Father's Day, to special, my father, or the things that I'm actually about, we just, we just going through how the the life happened from [age] 10 to 52.
AM: And you know. I don't want to, I don't want you to feel like I'm boxing you in with these questions. But I just wanted to get to this last one. As far as the you know that experience goes, I do want to ask you, what do you wish more people understood about the justice system, and could you talk to me about your show, uncuffed, and what you hoping to accomplish with that?
AS: Okay, so the show uncuffed was a pilot that, um, that I did maybe um, two or three years ago, and that pilot didn't get picked up. It because it was mostly about the relationship between community and policing and getting people to understand their rights and about how community, how policing in your community, should be, you know, I'm from a very unique situation. I'm I'm policed in the community that's policed by people from the neighborhood.
So, so that was the goal of uncuffed but, but that show didn't come to fruition, and we just released the pilot footage. It wasn't, um, wasn't a show that was actually picked up. And with the incarceration, I'm more concerned than getting people who were incarcerated, or doing things that could get themselves incarcerated, to explain that this is not a chance that you should take to put yourself in this, under this type of judicial slavery, and if you have been in that system, that this is you don't have to keep that persona of Being a prisoner. You know, you can, you can, you can rise from that mistake with educating yourself and mindset changes.
The Man…
AM: Ali, I want to ask how much of your success would you say was planned, versus how much would you say is destiny?
AS: I would say all of it is the blessing, because I had no idea how far I was gonna go in comedy. I wasn't looking for a ceiling. I was just looking to be a comedian.
You know, I was just, that was my my passion and my goal. So I wasn't, I didn't even get into this game 28 years ago, knowing that you can even make money from it. So that was, that was the thing, because most comics were that I saw were people who were in movies and sitcoms. It wasn't my life is a different life, per se.
I'm on the road, and I didn't know what road money looked like or those things, and then I'm also not for sale, so I am really in a different bubble than most comedians. You know, I don't live in LA or maybe New York or Atlanta because I'm not. I'm not actually chasing anybody else's, you know, Destiny. I'm not even judging myself according to what this person did, you know. And I want to do it too.
I just want to be a free, a free living individual and talk for a living, you know, versus I gotta get this I got people ask me, what's next? I'm like, I don't know. I have no idea what's next. And, you know, because everything that I'm passionate about comes to me in thought, and then I start to, you know, work towards that mission. But most of it is, well, all of it is just. Blessings from the Creator. I feel like it's just what's written for me.
AM: Now you're on your custom fit tour. So can you give us a little bit of a taste of what to expect?
AS: Oh, this is the third, this is the third 100 city tour.” [32:31] So the custom fit tour is not actually about the clothes. It's about people, people being in your life. Custom fitting people for your life. You know it's a more about who you who you surround yourself with, as far as in your growth and development as a as a person and as an adult, and not feeling bad about everybody that you've ever known that you thought that was supposed to be with you, and throughout the duration of your life, not being there because you you've changed, and some people haven't been beneficial to your change.
Most of my specials are unloading of all the old, past, bad habits and increasing the better habits that I had when I was being reared by my family, so shedding the streets and shedding those influences from outside of my family, you know. But I come from a pretty decent family, so I just went back to the values of what my grandmother, my mom and my uncles had and my aunts had instilled in me. It was just really reverting back to my true self.
AM: How does that feel for you going back to your true self? Does it feel like a custom fit?
AS: It's definitely, it's definitely a custom fit.
AM: Is there anything that you want to leave whoever's going to listen to the story with? What would you want to be their biggest takeaway about Ali Saddiq and who you are?
AS: I want to leave him with you are not your mistakes. Mistakes are things that happen. Who you are, as a true person, is different from your mistakes, especially if you don't, if you don't revert back to those mistakes, you learn from them.
AM: All right. Well. Ali Saddiq, thank you so much for your time. I really appreciate this interview, it was a great conversation, and I wish you the best of luck on the rest of your tour, and have a good rest of your day. Thank you so much.
AS: The pleasure is all mine. Thank you very much for spending some time with me. It was an honor and a pleasure.
In February, Ali won the 2026 NAACP Image Award for Outstanding Variety (Series or Special) for his comedy special Ali Siddiq: My Two Sons – marking the first time an independently produced and released YouTube special has been nominated or won a major award and it is the third most viewed special on any platform in the past year.
Seven of Ali’s specials are on Neilson’s “Top 50 Biggest YouTube Specials of All Time”
And in April, he took home three Webby Awards for his other special Rugged, released earlier last year.
Ali will be bringing his national Custom Fit tour to The Wilson Center at Cape Fear Community College in Wilmington, NC on May 2. Show and ticket info is available at www.AliSiddiq.com
