top of page

2022 WOMAN OF THE YEAR: THE QUEEN OF DAY: SHERRI SHEPHERD

EDITOR IN CHIEF & PHOTOGRAPHER: COREY GUEVARRA FOR CYOER PHOTO
HAIR: THEO BARRETT
MAKEUP: RODNEY JON
STYLING: CHANEL SMITH
STYLING: WILLIE SINCLAIR III

Sherri Shepherd for 26 Magazine Woman of the Year

Sherri Shepherd is a tour de force! Radio, television, film, standup, drama, comedy, you name it, she’s done it! If you’ve been anywhere on planet Earth this past year in particular, you’d also know that it was impossible to keep your eyes off of her as she soared into career milestones & ultimate dreams recognized! I think it’s safe to say, that Sherri Shepherd has had the BEST year ever! Her incredible career culminated into her lifelong goal, further confirming the ideal that success is in fact when preparation meets opportunity. The thing about opportunity however, that’s rarely revealed, is that often, even when it’s directly in front of you, you still have to actively reach up & grab it! Oh & did she ever, do JUST that! “Sherri” premiered on September 12th 2022 & quite literally, instantly became the #1 NEW talk show in the country! With the nation falling in love with her brand of ‘good feels’ she’s become a welcomed safe space, a breath of fresh air, a reprieve even, from the now usual harsher news & entertainment cycles. For the last 2 decades however, we’ve watched her build her career piece by piece, standing in the face of adversity, powering through & holding on to her dreams with tenacity, precision & authenticity! Through it all, she’s never stopped gifting us with laughter. If you’ve ever experienced her live, you’ll agree that when she leaves your presence, you remember her. The vapors of her genuineness & kindness linger like a hug from a good friend. Simply put, no-one is more deserving of a time such as this! This is our celebration of the incomparable Sherri Shepherd, then, now & forever!


Sherri Shepherd for 26 Magazine Woman of the Year

FROM THE OUTSIDE LOOKING IN 2022 SEEMED LIKE ONE OF THE BEST YEARS OF YOUR LIFE! WHAT HAS THIS YEAR FELT LIKE FOR YOU SHERRI?

You know it’s so interesting actually pausing to think about it! Sometimes between being a mom & the show & acting & all the other endeavors, the parts are moving, it’s happening, but when you’re in the middle of it, the observation of it all can feel so different. But in hindsight yes, 2022 has really been incredible for me! I think 2020 to now is still a bit of a blur for many of us, coming out of the pandemic, being able to guest host on Wendy, getting offered my own show, actually launching the show, working on a critically acclaimed comedy, moving to New York then having the show be SO well received? WOW, when you lay everything out like that, all I can truly feel is grateful.

TELL US ABOUT YOUR EARLY LIFE SHERRI:

I’m from Chicago Illinois & grew up in the city until my family moved to the suburbs later on. We moved to an all white neighborhood & of course back then they weren’t the kindest to black people. I remember that move well, specifically because it was right in the middle of when Kunta Kinte got his foot cut off. (Alex Haley’s Roots was broadcasting & everyone was watching it!) I Lived in Chicago until about age 17, when my parents got divorced we moved to California! The California move was pretty traumatic for me, my new high school was kind of segregated, all of the black students came from LA but I lived in the Valley, so making friends was basically impossible. It was my senior year, everyone else had their existing social groups & I was already a really shy person. I did end up making 2 good friends though, I had one friend that was a Prince impersonator [yes you read that correctly]. This was back when Prince & Vanity 6 were all the rage. I had another girlfriend, gorgeously beautiful, but she didn’t like her teeth, so she never smiled. Everybody figured that she was either conceited or perpetually angry. Neither was the case. Me? I was the dork funny girl & together we were like the three weirdos but I was so grateful for them. I always think about where they are today. -I’d bet that he’s probably in Europe somewhere, still impersonating Prince! :) After high school, I became a legal secretary, it was a solid job, but in my soul I KNEW there had to be more!

HOW WOULD PEOPLE HAVE DESCRIBED YOU AS A CHILD?

Incredibly shy, quiet, really really kind & loved to make people laugh. Now during my teenage years, they probably would’ve said I was very rebellious & honestly, I was! I used to climb out of windows & sneak out of the house while my parents were asleep, I was smoking cigarettes, following the wrong crowd! Thank God that He watches out for the babies, & fools because during those years -I was a fool! Ha!


Sherri Shepherd for 26 Magazine Woman of the Year
WHEN DID YOU DISCOVER YOUR LOVE FOR COMEDY SHERRI?

I think the very first time I got on stage. I initially remembered friends telling me that I shouldn’t pursue comedy, that it was going to take me 10 to 20 years to make it. At the time I was making $42,000 a year, I had pension & overtime & that was good money back then. They’d tell me, you have a great life, you have your own apartment, you’re only paying $500 a month, you’re good! But once they saw me perform they were also the same ones who later paid for my comedy classes. The very first time that I showcased & got on stage at a comedy club, the moment I first heard the roar of that laughter, I was hooked!

-SO IT WAS THE REACTION & THE CELEBRATION? IT WAS ALL THAT SHOWED UP FOR YOU IN THAT MOMENT THAT TOLD YOU THIS WAS YOUR PATH?

Yes, it was the laughing, the jokes about my real life scenarios that I couldn’t believe people found funny. I instantly fell in love with the feeling of euphoria that went through my body!


WOW.
WHEN DID STAND UP PIVOT INTO ACTING & HOSTING?

I think that started when someone asked me if I was taking acting classes. I’d been doing all the comedy clubs by then & they were like, oh well now you have to take an acting class! It was Hollywood, so everybody was in an acting class. Eventually I agreed & made my way to my first lesson. My acting teacher had a silver toupee, shirt opened down to his chest & a big gold chain around his neck. I remembered him saying “a lot of people in this room are not gonna make it, but there are some of you who are going to become stars” & he looked directly at me! Now I had just taken the bus to this class, I could barely afford it AND I got there late. I was honestly sitting in the back wondering why I was even there. But again he said, “some of you are going to become a star” & again he looked at me, this time pointing & said “I don’t know who you are, but you’re gonna be a star”! Of course I turned around looking behind me trying to figure out who he was talking about. But it was me & from there he always believed in me. Sometimes people see you before you can!

26 Magazine
WOW, IT’S INCREDIBLE HOW OTHERS CAN SPEAK INTO OUR LIVES UNKNOWINGLY & IF WE CAPTURE IT & WE BELIEVE IT & SUBSCRIBE TO WHATEVER THEY’VE TOLD US, A LOT OF TIMES WE’LL SEE THAT THREAD ILLUMINATE THROUGH OUR JOURNEY. BUT IT WORKS BOTH WAYS, FOR BOTH COMPLIMENTS & NON COMPLIMENTS. SO IT’S IMPORTANT THAT WE ONLY AGREE WITH THE THINGS THAT FEEL LIKE BLESSINGS. IT’S SO INTERESTING THE POWER OF THE TONGUE, THE HUMAN VOICE, HOW WE CAN LITERALLY CALL GREAT THINGS [OR NOT SO GREAT THINGS] INTO EACH OTHERS LIVES.

That is so true! The very first time I stepped into a comedy club was with my secretary girlfriend group. I’d never been to one before & prior to the show starting I was just telling jokes & having fun with the people around me. I’ll never forget when Andrew Dice Clay got up, he was making so many women mad with his material that this woman, literally I have no idea who she was, but she turned around to me & said ‘you can be funnier than that, YOU should be up there’! That sat with me all night. I couldn’t think about anything else, unbeknownst to her, she had planted a seed. For the first time ever, I truly wondered if I could do comedy professionally. I remember calling those same girlfriends, all 8 of them from that night & asked if they thought I could do stand up? 7 of them said no, but 1 said ‘if you don’t do it, you’ll never know’. I think of that night often, of that lady, that stranger in the audience, with a few simple words she changed the paradigm of my life forever.

LOOKING BACK, WHAT ADVICE WOULD YOU GIVE YOUR 26 YEAR OLD SELF TODAY?

Oh man. I would say that if you are just starting out in stand-up comedy, DO NOT, I repeat DO NOT sleep with any other comics!!! When you first start in this business, you are a new face, a fresh fish in the pond & all the sharks will try to circle. Especially when you’re young you can easily get caught up in all the new found attention. But please use me as a cautionary tale because it can take you 10 years to get your reputation back! Stay the course & again, stay away from the other comics!! I would also tell my 26 year old self that even if she’s scared of new opportunities, to just say yes! On the other side of fear is where so many blessings are & if you can just push past it, there are so many amazing things that are waiting for you. If you stay on the side of fear you never get to experience all the things that would’ve made you proud! There may be highs & lows along the journey, but so what? Do it scared, take the risks, it’s okay to leave your comfort zone!

YOUR LIFE IS COMPOSED OF SO MUCH COMEDY, SO MANY FEEL GOOD MOMENTS SHERRI, BY CONTRAST WHAT DO YOU TAKE MOST SERIOUSLY IN YOUR LIFE (LIKE WHAT’S THE THING THAT YOU DO NOT JOKE ABOUT?)

My son! Anybody who knows me knows you can mess around with Sherri, but do not mess around or let the ball drop with Jeffrey! Because my son has special needs, I try to be so diligent about his care & trying to equip him to live in a world that isn’t always kind to people who look like him. I’m always trying to figure out what more can I do, how can I be the best mother I need to be for him. It’s a constant battle of balance for me, deciding how much I can let go to let him explore, though all I ever wanna do is protect him from any potential hurt or harm. The hard thing about that is, we ALL get hurt. Hurt is also what can build us. As much as we try to shield from it, when it occurs it often teaches & expands us & gives us our muscles. That’s the hardest thing for me as a mother, I know I have to find a balance where he can also seek & have his experiences of independence as well.

YOU KNOW THEY SAY IF YOU CAN MAKE IT IN NEW YORK YOU CAN MAKE IT ANYWHERE. IS HE ENJOYING IT?

He is!! But sometimes he’ll come home & he’ll say ‘you know, I said good morning to people mom & they didn’t reply’! -As many of us know, New York is very different from California in the way that people in New York really just mind their business & are looking to get where they need to be. The California life he knows is a little more laid-back & if you say hello to somebody they’re generally gonna respond in kind. So the pace of the city & all the new personalities, he’s definitely getting used to. Complete transparency, I did NOT want to move to New York largely for that reason. I didn’t want to uproot him from his comfort zone & even for myself, my friends, my home base, they’re all in California & I tried everything I could, to do this talk show in Los Angeles! But don’t we all have that one prophetic friend? Ha! Well mine called me one day & said ‘girl I got a word from God for you’. She said ‘Sherri, God told me to tell you that New York is not for YOU, it’s for Jeffrey! That is where he will find his independence’! -When I tell you I was laid out on the floor, like anywhere but New York father please! LOL! I sat with that word though & suddenly all the reasons why doing the show in LA weren’t working out seemed to make sense. There was divinity at play & that insight allowed me to release all the energy I was using to push against this move. It simply wasn’t about me, this whole time it was about my son & him being able to have a life experience that will teach him new ideas of independence like never before!


Sherri Shepherd for 26 Magazine Woman of the Year
WOW. THAT’S HUGE, A HUGE PERSPECTIVE SHIFT!!

Yeah, you know that’s why I tell the people on my team that sometimes the blessings are not about one individual. That one person sometimes, is just a conduit God uses to bless everybody else around them. To me, the talk show isn’t just about me. It’s about the entire staff, all of the team members, it’s a divine appointment for all of us. So let’s maximize all the opportunities that are coming our way. When you leave this place after however many seasons we get to do this great work, if any of us leave here & are still in the exact same spaces we were when we started, then we haven’t fulfilled our full assignment as a team! So I’m constantly telling everybody, it’s about moving up. What else is inside of this blessing of the Sherri Show for you? Don’t be afraid to go & find what God has for each of you. You’re not here just to do my hair or my makeup this is about you too. Sure my name is on the door, but this is for everybody to be blessed by!

WHAT SORT OF LEGACY DO YOU HOPE TO LEAVE ONE DAY SHERRI?

Oh man! I hope that people felt like I added to their world because I made them laugh. I hope that when they were around me, they left feeling better than when they came. I think being kind is really underrated. It’s so important, especially now in this era that we’re in, I don’t think we have enough kindness & enough love & I think that we really have to be more intentional about them both. We’re all recently coming to terms with the death of tWitch. I never met him, but we can all clearly see the impact that he had. He had a light & we all felt it when that light turned off. -But the thing is, I think we all come here with a light as well & we just have to intentionally figure out how to spark it in one another! How do we turn it on, gift it, & spread it so everyone everywhere shines brighter while we’re here? I think that it’s in the little things, the smaller acts of kindness that you may not even know are making a difference. For example, I have a letter on my shelf from an audience member who wrote in saying that she comes to the show once a month. But fact that I come out before we start, to acknowledge everyone & say hi, It makes her day more than any other part of the show! -And you know I’m just coming to greet & maybe tell a quick joke & see everyone because I’m glad they’re there! I appreciate every single person that takes time out of their lives to come & partake in these moments with us. The fact that that small act touches any one person in such a way that they literally write a letter, (you know people don’t do that anymore) it just really speaks to the power of us simply being kind to one another.

IF YOU HAD ZERO COMMITMENTS, WHAT COULD YOU SPEND YOUR WHOLE DAY DOING?

You’d probably find me either walking 1 or 2 miles because I love to walk on a cool crisp day or you’ll find me in a park rollerskating, trying not to fall! If I’m staying in, you’ll find me in some fuzzy pajamas sitting on the couch, with the fireplace going, cozily listening to Musiq Soulchild or some Jill Scott, Teena Marie or Lalah Hathaway.

IF NOT THIS INCREDIBLE LIFE, WHAT ELSE DO YOU THINK YOU’D BE DOING JUST AS PASSIONATELY?

If I wasn’t “Sherri Shepherd” “the entertainer”, honestly I would still be doing some form of this even without the fame! Bringing people joy is what I believe I came here to do & it I think it would have shown up from me in one way or another. I would probably be calling up nursing homes bugging them to let me put on little shows for the residents. I’d probably find a way to mentor any youth interested in comedy, maybe by teaching classes at neighborhood centers. I’d literally be doing what I did before the fame came which of course was stand-up! The comedy I know, would be non-negotiable. Back in the day I was doing stand-up 7 to 10 times a week! Even after the fame I would still go to the comedy clubs, you know, the spots that only pay like $20 & you have to find your own parking somewhere in the neighborhood? But I would go because I still needed to get up on that stage & make people laugh! So definitely that, oh & dogs, I love dogs! I’d probably be volunteering at shelters & spending some hours per week taking care of dogs, hanging out with my furry friends while dreaming of opening for a Janet Jackson concert :)


Sherri Shepherd for 26 Magazine
IS THERE ANY ONE MOMENT IN YOUR JOURNEY THAT YOU WOULD GO BACK & CHANGE OR RE-WRITE?

Probably the times when I talked myself out of doing potentially great things. Especially back then when I had the energy to do it! You know as you get older, you may be willing but the energy is different. It’s just a natural part of life. They say 50 is the new 40, sure, but your body is still 50 years old! LOL. So sometimes you don’t have the energy or the stamina that you did when you were younger. Like I would love to write. I’ve had so many scripts & amazing ideas in my head that I knew would be funny on the screen. But I just never completed them because I always listened to that little voice that said ‘oh you’re not a writer, who do you think you are? You don’t know wordplay, you didn’t go to school for this’. So I just never finished any of them. I wanted to write a book about the women in my family & again, that little voice kept saying ‘you’re not an author, who are you to write this book’. Fast forward to now, consequently all of those women are now gone, they’ve passed away & I never got to partake & document the knowledge they possessed because I was afraid. I will say however, that I’ve made peace with any opportunity I “seemed” to have missed. There is divine timing, I’m still here & I think it’s better to focus on the millions of blessings that DID happen, all the incredible things I absolutely did do!

I OFTEN SAY THAT EVERY DAY THAT WE WAKE UP WITH BREATH IN OUR LUNGS IT MEANS THAT WE STILL HAVE PURPOSE. IT MEANS THAT IT’S NEVER TOO LATE TO DO ANYTHING!

Omg! I was just having that exact conversation with Niecy Nash. I’ve had it with Garcelle Beauvais & other girlfriends that are similar in age. We’re all in our 50s now & we’re all ‘like who would’ve thought that this type of success would’ve shown up at this age as opposed to when we were in our 20s & 30’s. If this sort of success happened then, we would’ve been hot to trot! LOL -But it’s happening now & maybe we needed to gain this wisdom first. I tell Kym Whitley all the time, at this age so much is coming & maybe God needed us to slow down, sit down & appreciate it so that we also would know the importance of opening the door for others as well. Maybe we wouldn’t have done that in our 30’s because in the limited experience of youth we often make the mistake of thinking that everything is about us. Listen, God knows that if he would’ve given me this in my 30’s, by now, y’all would’ve been like ‘what ever happened to that Sherri Shepherd’ LOL -I would’ve probably been an E! true Hollywood story!

WHAT ADVICE WOULD YOU GIVE TO ALL THE FUNNY, SMART, INCREDIBLE GIRLS, BLACK GIRLS, BLACK WOMEN WHO WANT TO FOLLOW SIMILARLY IN YOUR FOOTSTEPS?

I would say find somebody who is doing what you want to do & bug em, bug em, bug em, until you get on their nerves! Ask if you can just meet with them for 1 hour so to pick their brain! Get mentors, I wish I would’ve done that. Earlier on I was kind of an island unto myself, but now I understand the value of asking questions & getting advice from people who are doing or who have done what you’re setting out to do. Now I’ll send a clip to Oprah & ask her what she thinks I could’ve or should’ve done differently. Ask about the career path & what balance looks like, I asked Oprah & she had an earful for me! She said a lot of balance starts with you also saying no sometimes. I had never even considered that perspective. So get mentors & ask questions, you don’t have to go at your goals alone.

OUR LAST QUESTION, OUR FAVORITE & STAPLE QUESTION AS OVER THE YEARS THE ANSWERS HAVE RANGED TO EVERYTHING FROM ITEMS TO EXPERIENCES. FOR MARIO LOPEZ IT WAS “CIGARS”, FOR MEHCAD BROOKS IT WAS “THE FREEDOM TO DO WHAT YOU LOVE” FOR US AT 26 WE DESCRIBE LUXURY AS A STATE OF MIND. SHERRI SHEPHERD WHAT’S YOUR DEFINITION OF LUXURY?

I remember as a kid saying that I would never wear Payless shoes again! At the time Payless & other less expensive places were all that my parents could afford. Of course I was grateful, but, I’ll never forget how much those shoes would hurt, make my feet sweat, I’ll never forget how they smelled & it always sounded like something was rattling around in the heels LOL. I said one day I want to be able to shop & not even look at the price tag. So today when I’m able to go into a store & buy a pair of shoes that I love, that are comfortable, I do it for the little girl who couldn’t, who endured the physically painful, sometimes embarrassing footwear growing up. That’s luxury to me, being able to create moments of redemption for my younger self. Additionally, just before Covid, I flew 31 of my family members out so we could all have Christmas together, I wanted everyone to be able to see their legacies. It cost a pretty penny, but that as well is luxury to me, being able to do things & create once in a lifetime experiences for your loved ones. Money can always be made again, but the time we got to share with one another, experiences like that are priceless!


SHERRI SHEPHERD, THE EXPERIENCE OF YOU IS PRICELESS. THANK YOU FOR SHARING YOUR UNIQUE, COMEDICALLY INTELLIGENT, STUNNINGLY BRIGHT, UPLIFTING LIGHT WITH THE WORLD! WITH LOVE,
-26.
R E C E N T  P O S T S
A R C H I V E
F O L L O W  U S  !
bottom of page