I had the distinct pleasure of interviewing Mike E Winfield. His comedy is refreshing and relatable in a way that makes him a comedic genius. Hailing from Baltimore, Mike E Winfield moved to California to pursue comedy and to escape the rough streets of Baltimore, remembering how he found a gun under his mom’s pillow as a child and thought, “I can’t wait for my teeth to fall out.”
The comedy scene felt natural to him, and he embraced it raking up credits such as The Late Show with David Letterman, a re-occurring role on NBC’s The Office, Brad Paisley’s Comedy Rodeo on Netflix, an Emmy nomination and multiple movies in post-production, one with the rapper DMX called PIMP. Somehow in the midst of rising to the top, he had to grow up quickly because he fell in love and married an older woman with a child.
That was actually the problem. He wasn’t ready to be a husband, so he made many mistakes with the marriage. He has since learned and developed a bond with his stepson, whom he jokingly refers to as StepMAN because they’re close in age. He takes his ups and downs in his life and marriage and turns them into jewels he releases on stage.
He often jokes about the age difference and his wife treating him like a kid. For instance, in the grocery store she yells in front of everyone, “You better not throw anything extra in the shopping cart.” His response? “Well that’s hard for me to do while I’m sitting in it!!”
Thank you so much for doing this with us! Our readers would love to get to know you a bit better. Can you tell us the story of how you grew up?
You know that one show called The Wire, well I grew up on the other side of that town in East Baltimore. In seventh grade my mom and dad decided it wasn’t going to work out and he moved back to Sacramento to be closer to his side of the family. I had a fun childhood, I had lots of friends. This was during a time when kids used to hang outside and play pickup football or basketball at a nearby court. On the court, they use to say I was “nice!” “Shorty nice.” That’s a term in the inner city when you have basketball handles and a silky shot, which I had even if I dribbled too much. It was myself and my younger brother who has always been more mature than me. My mother worked long days to provide for us and did a great job. That motivated me to always keep cash in my pocket. I would save all of my birthday and holiday money. At 16, I got a job, working at Burger King. I thought I was rich. I was also driving, dating and cutting class. Cutting class didn’t matter to me, I could still comfortably hold a B average. I figured that would be good enough to get me into a college. After graduating high school, I moved to Sacramento to live with my dad. I transferred my job so I was still working, and I enrolled in Sac State university. My mom and dad thought I had so much money they made me put myself through college.
Can you share a story with us about what brought you to this specific career path as a comedian?
In Baltimore, we used to spend the night at my cousin Damian’s house for some weekends. It was actually his parent’s house. We used to hang in the basem*nt and pull all-nighters. One night, he was like I want you to see something, and he put in a VHS Tape of Eddie Murphy’s RAW. As a super young kid, I remember thinking WTF am I seeing right now. It was unbelievable this guy in these weird clothes is speaking so freely and making fun of people that I had respect for like Mr. T and Michael Jackson. I asked my cousin, “Does he get paid for that?” My cousin looked at me and laughed like he always did when I asked stupid questions. I just couldn’t believe there were other options out there besides being a doctor, lawyer, or teacher. That’s when I first knew.
Can you tell us the most interesting story that happened to you since you began your career?
This is definitely subjective because there’s so many, but I’ll pick one and save the rest for my own book that I’ll have published by the start of the year. I was selected in an HBO comedy festival as part of the LUCKY 16 for unheard of up-and-coming comics. I’m walking through the Caesars hotel with comedian Russell Peters. At the time, his brother Clayton is managing me and I’m almost 4 years into comedy. I’m also on fire as far as exposure goes. On stage, I’m at an undeniable confidence which no one should have at almost 4 years in. It’s dangerous. While we’re walking through, we bump into Craig Robinson. Craig starts beat boxing and people start surrounding him, first its 4 people then its 17. Next thing you know, over 20 of us are walking through the hotel taking turns carrying the beat. It’s insane!! So much fun!! We bump into comedian Bobby Lee. Russell introduces me to Bobby. Bobby and I chit chat for about 90 seconds tops. No more than that, I promise. Fast forward, a week later. Clayton tells me that Bobby Lee wants me to play his best friend in his pilot for Comedy Central. What the f*ck!!! He and I spoke for no more than 90 seconds then went our separate ways. Anyway, I’m terrible in his pilot, showcasing zero acting skills. It’s possibly why no episodes were ordered. Til this day, Bobby says I owe him. I think he’s joking, and I also think he’s serious.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
I was so fired up. I was on one of my first comedy road trips to Oregon. I was set to make about $200 for a week-long trip. I felt like the king of the world. I’m traveling for standup comedy. Don’t say anything to me!! I’m opening for Del Van Dyke and rolling with a guy named Dave Bothun. Dave and I started at the same time and used to MURDER the open mic every Wednesday. No one could stop us. We didn’t go to the open mic, we WERE the open mic. We arrive at our 2-star hotel and I’m in comedy heaven. Dreams do come true! We show up for the 8pm show around 7:30. There’s a lot of people in there, it’s a dive bar. I’m unbothered, remember I’m the king of the Sacramento open mic. Show begins, Dave is hosting, I’m the middle act and Del is headlining. Dave goes up, he’s doing ok. I’ve seen him do better. It’s his first road trip too, I can’t put together why it’s not going as great for him like I’m used to seeing. Nevertheless, I’m going next and I’m going to rip this place to shreds because I’m the king of the Sacramento Wednesday night open mic. I’m up, at this point my intro is, “He’s funny and you’re gonna love him.” This is before the E. “Give it up for Mike Winfield.” I go up. Joke one, it crushes. Joke two, flop. Joke three, flop. Joke four flippity flop. I’m supposed to do 15 min, I’ve used my greatest hits and I’m currently 4 min in. I abandon ship!!! One thing I’ve always done is audio record my sets. After listening, what happened was I did ALL Sacramento local references in Medford, Oregon. They didn’t give a damn, nor laugh. It was a painful set. Del goes up and kills it and I start drinking beer.
Lesson: Don’t do local jokes if you’re in another city.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
This guy has burned so many bridges in the industry, he personally told me not to mention his name on my way up so no one takes away an opportunity from me. I told him I couldn’t comfortably do that. I’ve always received a lot of love in the business, but he was the first to tell me I was a star. I didn’t know what it meant at the time. He was the first to correct mistakes I was making. Comedian Willie Barcena took me under his wing. He showed me a proper work ethic. NO OTHER COMEDIAN was working this hard. I learned that this is what it takes to see results. I also picked up bad habits as well, he’s a heavy drinker and in the environment, I also became a drinker. He offered tough love and zero excuses. He told me I was LeBron because I had all the aspects for greatness, and he was John Stockton because he would always have to work a little harder lacking comedy athleticism. I’m incredibly grateful for that time and those couple years we worked together. Along with comedy, he threw in life lessons. Our relationship is interesting to me because he contains every trait of my actual dad. Good and bad.
You have been blessed with great success in a career path that can be challenging. Do you have any words of advice for others who may want to embark on this career path, but seem daunted by the prospect of failure?
Advice? Standup is evolving at a rapid pace and making some unusual shifts. My advice used to be 1. Don’t procrastinate, start yesterday and make no excuses for putting it off and 2. Get on any and every stage you can find so you have balance. If you go to only one place, it can restrict your ability when entering other rooms and or regions.
You have such impressive work. What are some of the most interesting or exciting projects you are working on now? Where do you see yourself heading from here?
First of all, Thank You! I have a few fun things in play. One is I’m planning to host my own talk show, but it has a very specific premise that I can’t share because I’m currently pitching it and don’t want to give it away. I also have over 3 scripts of a sitcom titled STEPMAN, based off my standup which feels inevitable when some company is ready to become billionaires. I have one movie written, but I don’t really like it, so I’ve started another one. I think I was so bored during quarantine that I experimented on scenes and characters and wrote something that was funny to me at the time.
I definitely can see myself being cast in more television and I’m ready to record a standup comedy special. It’s currently 42 minutes and it lives in my head and it’s all brand-new unheard of material if you haven’t seen me in 2 years. It’s funny to me and most of all, fun, personal and silly at times. It’s the kind of comedy I love.
What do you do to get material to write your jokes? What is that creative process like?
Ok, hear me out and don’t take this the wrong way. So, part of why I’m a genius is because I take enormous risks on stage. I apply the belief that the bigger the risk, the bigger the reward. It’s like, “If I can get this joke to work…” I challenge myself to new levels of creativity that even top what I’ve done last. I can sit down and write. I do it daily and I play my own audio sets as background sound, and I write while listening to “that guy.” I try at least 90% of what I write in my book even if I don’t think it’s funny anymore just so I can see what happens. I’ve found over time that I’m funny in ways that I didn’t quite understand, so I don’t have to overdo the delivery even though I’m naturally big and captivating. When I know it’s funny, I add some extra performance and now in my later years of standup I enjoy acting out every single piece.
Super. Here is our main question. What are your “Five Things I Wish Someone Told Me When I First Became A Professional Comedian” and why? Please share a story or example for each.
- I wish someone would’ve told me that you will be forced to choose between having a family and achieving greatness. In the beginning as a standup, balance is overrated. My wife understands now, but I made selfish decisions to take low paying gigs because I had to enhance my skill that I believed would eventually payoff in bigger ways. I feel that it’s not responsible for me to advise anyone to follow in these footsteps, it’s just something that’s in you or it isn’t.
- Be honest with the stage, with yourself and everyone who cares about you. Comedy is definitely subjective, and many comedians are delusional. The more you understand that there’s a lot of necessary growth, the more you’ll discover the results that you can gain. Sometimes I would do the same joke, the same way, for 5 and 6 times and think the crowd was the problem. No, the problem is the joke and when I can be honest about it, it will evolve.
- I wish someone would’ve told me how dangerous the misuse of social media could be. There were so many posts that I thought were simple, but in fact were hurting my relationship and people around me. In time, you learn to adapt and be the version of yourself you actually want to be. I wish someone would’ve said, “Don’t post that, definitely don’t post that. Hey man, give me your phone.”
- I wish someone would’ve told me to collect every contact and email from fans. Those numbers add up. I used to collect emails and then eventually I got lazy and figured they would remember me if they wanted to. This is a numbers game sometimes and you have to keep that in mind.
- You’re going to get offered a lot of things when you’re on the road and you’re allowed to say no. It’s easy to overindulge with alcohol and that’s exactly what can happen when you’re in different places and everything is free. There were times I was only trying to be nice, but that put me in situations that I had no business to be involved in.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
My biggest inspiration growing up was my mom telling me I could do anything in life. She made me believe that and I do. I’m often told that I inspire, but I think I genuinely need people to understand that there’s a proper approach for achieving all goals but believe in yourself and pursue it. Don’t do anything at the expense of your family, but if you keep your responsibilities lower in life, then it’s ok to take a few career risks. “There’s nothing you can’t achieve.”
You are a person of huge influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?
I would say nutrition. We put so much trash into our bodies and because of it, we live with so much disease inside of us. My approach would be that you don’t have to give it all up in one day. There’s a path to a happier, healthier you.
Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!
It would be cool to have lunch with Jordan Peele. I know he comes from the standup world and I remember watching him and Key at a festival and other stages. I feel like he goes against the grain in film and everything I want do in creating is off the beaten path as well. I want to create dark dramas with hilarious turns. I want quality suggestions and great perspective to make a piece of art that moves the viewing audience, I feel he could offer that. People still talk about Get Out. I feel like my energy and demeanor pairs well in that world.
Are you on social media? How can our readers follow you online?
Yes!
https://www.instagram.com/mikeewinfield/
https://www.facebook.com/DesirableMike/
https://twitter.com/mikeewinfield
https://www.tiktok.com/@mikeewinfield [tictok.com]
This was so informative, thank you so much! We wish you continued success!
