Caitlin Dobbins, a senior musical theatre major, is no stranger to live performance.

Dobbins will take on the understudy role of Pamela—otherwise known as the most beautiful woman in all the land—in the jukebox musical comedy “Head Over Heels” with the Chicago-based theatre company Kokandy Productions.

Playing through Aug. 25 at Theater Wit, 1229 W. Belmont Ave., the show—which is based on “The Countess of Pembroke’s Arcadia” by Sir Philip Sidney—takes place in the 16th century and is set to the music of the ’80s all-female, new wave band the Go-Go’s.

Dobbins spoke with The Chronicle about her role in the new production, her experience with plays and musicals and what it is like to balance her theatreworkload on top of school.

THE CHRONICLE: What is “Head Over Heels” about?

This show actually is very dear to me. All the music is from the Go-Go’s and one song is [an] original. It talks about gender and sexuality and how … labels don’t really matter. We have a non-binary character… a same-sex couple … a straight couple. It talks about gender and sexuality throughout the show. 

The show is [about] love. it’s really good that around this time, especially [with] what’s going on in America, this show is very needed.

What is it like to be in an ensemble?

I am understudying Pamela, which is one of the sisters in the show. The show is very ensemble driven, and basically they tell the story throughout the whole show. It is a lot of dancing and a lot of being vocally ready for the show. The ensemble is not just random people in the back, not just random people walking around. We push the show; we help tell these people’s stories.

What is your favorite musical number and why?

It has to be “Get Up and Go” because we do this cool suitcase bit. It is really cool, and after every time we do the suitcase bit people freak out. “Vacation” is also a really cute number. One of the leads goes to this vacation spot called “Lesbos,” and it is basically an all-gay couple retreat, and [is set to] “Vacation” by the Go-Go’s.

How was the first week of production compared to now?

We were trying so many things out the first week. It was always a very comfortable area and very interactive. My love for these people has not changed since day one, but the way the show has changed and has grown … has gotten so much better, has told the story even more. The arc of the show has changed so much. If you watch the show the first day of rehearsal and see it now, you would think it is two different shows.

What is it like balancing schoolwork and the productions you are in?

It is rough. I have to be very organized. At the end of the day, I feel like theatre is always going to be here. Theatre in Chicago is always going to be here, but … you have to have a degree [because then] you can do any type of work. I have to put my priorities first, and I have to make sure my grades are still up to par while still working on-campus and making sure I still get that bread. It is worth it because, 10 years from now, I am going to look back and be happy I did it.