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We Adore Her


Playboy New Zealand Cover Feature May 2021

with Sydney Wilder

Photography by Caleb Chic

Hey Sydney, tell us a bit about yourself – background, your brief life story and career so far, etc… I attended the American Academy of Dramatic Arts, The Groundlings, UCB, Second City and I graduated from Second City’s prestigious writing program. I started doing stand-up when I was 19. I transitioned out of stand-up at 23 and I got into character work plus sketches within the social media world. I have produced, directed, written and starred in several viral videos that have amassed millions of views. My view count for my content including collaborations is over HALF A BILLION. My comedy work has been featured in Cosmopolitan, Funny or Die, Comedy Central, TBS, Huffington Post and Nerdist. I’ve worked with top comedians such as Andrew Dice Clay, Adam Carolla, Bobby Lee, Brad Williams, Adam Ray and countless others. I’ve performed at The Comedy Store, The Improv, Flappers and Helium Comedy Clubs. I produced a successful sex-positive, comedy and mental health podcast with guests ranging from Jim Jeffries, Margaret Cho, Mental Health professionals + other celebrities and influencers. It’s been listened to on 6 of the 7 continents and has charted all over the world. My modeling work has been featured in Playboy, Maxim, FHM, Sports Illustrated, Askmen and now MyTextDaily to name a few.

Do you have any nicknames? What do your friends call you? My friends call me both Sid and Sydney.

What’s the best thing about your hometown and why? I moved to Los Angeles when I was 16. I honestly don’t remember much from my hometown. Most of my formative years happened in Los Angeles. If I had to answer I would probably say the kindness of the people in Georgia. That southern hospitality is not as prevalent in Los Angeles.

Tell us about this shoot – where, when, what you enjoyed about it, etc…? I always enjoy working with Caleb. We shot this in April 2021. He finds the most interesting locations. I loved the olive oil spray that was infused with coconut oil!

How did you get into modeling? I used to sneak out of my house to dance battle in Atlanta. One night I won tickets to a concert in Atlanta and there were photographers there that asked me if I considered modeling. That thought never crossed my mind and here I am more than half my life later.

What’s been your career highlight thus far? My career highlight would be dominating Daniel Tosh on Comedy Central’s Tosh.0.

What’s the best thing about having Instagram as a tool? I can’t name the best thing about Instagram but I can confidently say that I’m grateful to have that platform to connect with others, share my work, pieces of my life and random thoughts in my head.

How do you usually deal with negative criticism from followers? It honestly just depends on the day. Some days I use it as fuel to motivate me or a comedy bit and others it kind of hurts.

What are the best and worst things about being a model? The best thing is getting to feel sexy and powerful. As a former fat kid, I find that to be very empowering. The worst part is when you post a hot photo on Instagram and people expect you to look like that all the time. I don’t look good at every angle or in bad lighting. And I certainly look different without my makeup on.

Do you have any guilty pleasures? Food? Bad comedies? The real housewives is probably my guilty pleasure. I love New York, New Jersey, Atlanta, Salt Lake City and Beverly Hills is OK.

Favorite movie quote? When I’m good I’m very very good but when I’m bad I’m better – Mae West in I’m No Angel.

Favorite travel destination? Capri, Italy.

What’s the first thing you think about when you hear the word ‘Playboy’? Sexual freedom. I am honored to be a part of a magazine that has led the way for women to embrace who they are in their own skin.

What would you say is a common misconception people have about you? People think that I am one-dimensional and purely a sexual object because they’ve seen my body. I do my best to fight that stigma but it still exists.

If you could live anywhere in the world, where would it be and why? I’d probably have a house in Malibu and a big condo in West Hollywood.

What’s the best way for a man to win his way to your heart? Be kind, patient, confident but still vulnerable and generous.

What’s one thing you wish guys understood about women? We don’t all work the same.

What’s one feature you absolutely love in a man? It’s hard to name just one. I find a man who is a great communicator to be very sexy. A man with manners, who respects and accepts where I’m coming from is also important to me.

If you took Playboy on a date, where would we go and why? Well, since it’s Playboy I’d have to take you to Mistress Justine Cross’s Dungeon East.


DoB: September 26

Height: 5’8

Eyes: green

Bust: 34C

Location: Atlanta, Georgia