A life in the theater | For out actor Michael Rupert, ‘Legally Blonde’ is the latest stop in a career that spans half a century

Michael Rupert would just like everyone to know that he really is a nice guy, at least offstage.

The Tony Award-winning actor has played plenty of “bad guys and charming jerks” throughout his accomplished stage career. Now at 58, Rupert is in the national tour of “Legally Blonde” the musical, recreating his original Broadway role as the scheming, nasty Professor Callahan.

“I kind of do those roles really well, but I’m not that kind of guy at all,” Rupert says by phone from San Jose, Calif., during a tour stop. If WiG’s conversation with him is an accurate reflection, Rupert is indeed a nice a guy and a gentleman as well.

Rupert makes his home in New York City with his life partner of 12 years, Will Chafin (who’s in the music business). Rupert’s one of those rare actors who remains steadily employed – both on and off Broadway. He received his first Tony nomination for his first Broadway show at the age of 17, for the Kander-Ebb musical “The Happy Time.”

“I was just fortunate,” he says humbly. “I’ve been doing it (acting) for a long time.”

And that he has.

Rupert grew up on the other coast, in Los Angeles near the Pasadena Playhouse. “I asked my parents if I could be in an acting class and they were very supportive,” Rupert recalls. “I think they thought I’d do it until I went to college to become a dentist.”

Rupert was “discovered” doing a show at the famed playhouse, playing the young boy role in Jean Kerr’s “King of Hearts.” An agent saw him and asked to represent him.

“My first job was in a professional production of ‘Peter Pan’ in Los Angeles playing one of the Lost Boys. Vincent Price was Captain Hook,” he says. Film actress Janet Blair played Peter Pan.

With an agent and equity card in hand at age 12, Rupert went on to work in television during the 1960s, with roles in “Marcus Welby, M.D,” “The Waltons,” “My Three Sons” and “The Partridge Family,” among others.

When legendary Broadway director and choreographer Gower Champion couldn’t find the teenage boy he wanted to star in “The Happy Time” on the East Coast, he and writer N. Richard Nash set out for Los Angeles to scout talent.

“I literally was the second to last person they saw,” Rupert recollects, adding that about 1,000 young men were seen for the role. Although the role landed Rupert his first Tony nomination in 1968, he would have to wait until 1986 to win the award for his featured role in a revival of “Sweet Charity.”

Rupert went on to star in a number of Broadway shows, including “Pippin,” “City of Angels, ”Ragtime” and what he calls his favorite but most challenging role, Marvin in William Finn’s “Falsettos” (Also in the original cast was Whitefish Bay native and Broadway veteran Chip Zien).

“That role was an enormous amount of work and hard,” Rupert recalls. “It’s all about family – these flawed, passionate, loving people. It was a real joy to do.”

Rupert played a man who leaves his wife and son for another man, resulting in both drama and humor as they all learn to coexist.

During the time of his “Falsettos” work in the 1980s and ‘90s, the HIV/AIDS epidemic was spreading through the entertainment community. Rupert knew a number of people who succumbed to the disease, including a close friend. So, doing Falsettos became more than just another play for the actor.

“It’s a story about a family, not just gay people,” Rupert emphasizes. “It was a very moving experience for me.”

As the adult male figure Prof. Callahan, Rupert faces new challenges.

“After the first week of rehearsals, I turned to our director Jerry Mitchell and said, ‘Practically everybody in the cast could be my child.’” That’s actually a good thing for Rupert because, as he points out, “their energy in rehearsal is just bouncing off the walls.”

And being around such a young cast also reminds Rupert of the times when he was just starting out in the business. “It really sounds corny, but it reminds me of why I got into the business a long time ago. There’s the joy – and the energy – of being on stage eight times a week.”

“I hope that (the audience) is surprised by the show, with a story that is as sweet as it is,” Rupert says. “The truth is, with the storytelling, the staging and the acting, I hope they’ll be surprised by how smart the show is as well.”