WHYY’s Cherri Gregg Talks Her Badass Husband, Wawa, and R. Kelly Regrets

Cherri Gregg of WHYY / Photograph by Stevie Chris

Cherri Gregg wanted to be a lawyer. Then became one. And then she decided that she really didn’t want to practice law. All of that worked out in our favor, because Gregg made a career leap into radio. She worked at KYW for years and now co-hosts a Best of Philly-winning show on WHYY. Here, Gregg explains how she could have been named “Collard” and why she’s no longer a cat person.

My first name is pronounced … cherry, like the fruit. When my mom was pregnant, she could only eat cherries and collards. She was going to name me one or the other and fortunately didn’t choose Collard.

I’ve lived in Philly since … 2008. Grew up in D.C. and Maryland, went to Atlanta after graduating Howard’s law school.

I ditched the legal profession because … I originally went into it only because I wanted money. When I was a kid, I loved to get people’s stories. I would walk around the house with a hairbrush for a microphone and make people tell me their story. So after doing law for a bit, I did some introspection and decided to pursue my ultimate dream: broadcast journalism.

These days, I live in … East Kensington/Fishtown.

If you want to hear me on the radio … listen to “Studio 2.” The show is talk radio meets NPR. My co-host, Avi Wolfman-Arent, and I are very conversational. It’s like your friend telling you the news but with the integrity of NPR.

Being a journalist in 2025 is … tough, because we’re competing with influencers who aren’t held to any standards and because of all the threats to the First Amendment.

My big plans for this summer include … going on my honeymoon. We were married in March at City Hall. He spent 26 years in the Marine Corps, did 13 tours. He’s a bona fide badass. He lived in Japan for seven years, and we’re honeymooning there in August.

To stay in shape … I run on the treadmill, lift weights, and ride my Peloton. We have a whole gym in our basement.

If you look at my high school yearbook, you will see that … my high school sweetheart and I were named cutest couple.

The first pet I ever had was … a cat named Lucy, but she was crazy, which turned me into a dog person.

My secret junk food obsession is … that trail mix with candy. It’s like, here’s some healthy stuff and protein, and then, oh yeah, here’s some M&M’s and dried fruit covered in sugar.

When I want to relax … I meditate. I’ve recorded my own affirmations.

A bad habit I cannot break is … cracking my knuckles. I don’t even know why I do it.

My first big concert in life was … R. Kelly in the ’90s. He was on a big bed in the middle of the stage. Looking back, I’m wishing I hadn’t seen that.

If you’re making me a drink, I’ll take … anything with “-tini” on the end.

One thing you may be surprised to know about me … is that I’m a gardener. I’ve fallen in love with the process of gardening and getting my hands dirty. People are shocked. You have a garden?! Yes, I do!

The movie I’ve watched the most times is … The Color Purple. The original. I tried my best with the musical version, but no. I applaud them for trying. I really do.

My go-to karaoke song is … “Push It.” Believe it or not, we did this at my Catholic middle school or elementary school. Dressed up as Salt-N-Pepa and everything.

At Wawa, I generally get … Colombian coffee with a splash of French vanilla. If I’m getting food, it’s a couple of boiled eggs and a banana. I’m so boring!

I get my hair done at … Graceful Style in Germantown. Gracie is so good!

Of the Poconos or the Jersey Shore, I will take … the Poconos. Too many rules at the Jersey Shore. I don’t like the vibe.

If I had to describe Philly to an outsider as briefly as possible, I would say … a hard nut to crack, but once they love you, they love you.

Published as “One of Us: Cherri Gregg” in the June 2025 issue of Philadelphia magazine.