Chester Gregory Recalls His New Edition Obsession and Looks Forward to Dueting with Lillias White at 54 Below

Chester Gregory, best known for his stage appearances in Sister Act, Dreamgirls, Hairspray, Tarzan and Cry-Baby, brings an intimate, new concert The Eve of Jackie to 54 Below on February 4. The concert explores and celebrates the life of Jackie Wilson and will feature a special guest appearance by Tony winner Lillias White. Below, Gregory reveals his obsession with New Edition, his favorite musical theater songs and the popular break-up song he recorded.

What record/album was your favorite growing up?
Several albums by both Michael Jackson and Prince.

What concert most influenced you as a performer?
New Edition/BBD. I thought I was the ghost member of that group—I knew every step, word and inflection.

What is your go-to audition song?
Usually a song from a previous show I was in. It's somehow always appropriate.

What song are you most excited to perform in your show?
"No Pity (In The Naked City)." It will be my first time performing this song.

What musical theater track is the most played on your iPod?
The Wiz original Broadway cast recording and Jesus Christ Superstar. I can sing every song all the way through.

If you can invite any performer on stage for a duet at 54 Below, who would it be?
I'm honored to be doing a duet with the great Lillias White. How could I ask for anything more?

What musical theater performer from the past do you wish you can collaborate with?
Michael Peters. His work is pure genius.

What album was the soundtrack to your 20s?
I'm not in my 20s?

What is your favorite workout track?
"Lyrics To Go" by A Tribe Called Quest.

What’s the best hidden gem in on your iPod?
Georgia Anne Muldrow!

Favorite break-up song?
I don't have one, but people have told me they relate to a song I released a few years ago called "Questions". I sang through the pain when I recorded that one.

What song most makes you smile?
"I Never Learnt To Share" by James Blake.

When this song plays, I can’t help but dance:
"It's Just Begun" by Jimmy Castor Bunch.

Check out Chester Gregory’s The Eve of Jackie on February 4 at 54 Below. Below is a video of Gregory performing the song “To Be Loved” live.