Leonard also has recorded and produced most of Rockapella's recent albums, including "Smilin'," a summer-themed recording, and last year's "Comfort and Joy," a Christmas-themed album.
"It's Rockapella for your whole year," says Leonard.
"Smilin'" is about "half original and half summer-themed covers," he adds.
"We do half and half. It's a good blend. We really enjoy picking songs we enjoyed as kids or love now, and do different treatments.
"Rockapella had time to develop a signature sound, and it's fun to apply that to songs people know. We haven't shied away from (others' groups). We do doo-wop, '50s and '60s oldies. And I write songs - I've developed a songwriting career for myself. It gives us a certain legitimacy within the music world. We're not just entertainment."
Colorful, far-flung history
Rockapella started in the mid-1980s with a group of college students who went to New York City, where the group is based, and sang on the streets. Leonard, who originally is from Indianapolis, now lives in Tampa, Fla., with George Baldi in Orlando, Fla. and Kevin Wright in Winter Haven, Fla. Jeff Thacher and Elliott Kerman, an original member of Rockapella, both live in New York.
Leonard attended the University of Tampa on a baseball scholarship, but also furthered his experiences in music there.
"I think I always knew in the back of my head that I was not good enough to be a major league baseball player," he says. "I really wanted to be Elvis or Prince or Michael Jackson. Music was always kinda my real love. My mom and dad were musical, and I sang at church and sang in school groups sometimes."
He says he was in denial about music as a legitimate career choice, but started considering it more seriously during his college career. From Tampa he went on to Disney World in Orlando, then the Disneyland in Tokyo, and pursued music there.
"I fell in love with that country," Leonard says. "I was there to make records, and I fell in love with the country. I remain active in the recording industry in Japan."
But returning to New York appealed to him, and he answered an ad in Backstage, a trade publication.
"So I came back to America," Leonard says. "The ad was for Rockapella, and I thought I'd do it for a little while. It was 1991 when I joined.
"Then the group started with the TV show 'Where in the World is Carmen Sandiego?' Suddenly, we were a national act. Before that, we did parties and bar mitzvahs. But because of the TV show, there were no more bar mitzvahs."
"Carmen Sandiego" was a mostly good opportunity for Rockapella, but it pigeonholed the group.
"When I joined Rockapella, I hooked (the group) up with Japanese recording deal. In America, we only had kids deals, like 'Carmen Sandiego.' ... But Japan is more open - the music world is more open. There are different types of music. So, we got a record deal there and released several records before we had a record deal in America. It was not until '98 in America that we got a record deal. And it's kinda interesting how we got that.
"Rockapella had been a successful commercial jingle career since its inception. It had done a tasteful job, done a variety and gained exposure from that (commercial jobs)."
And that exposure led to the record deal.
"We started making records and releasing them," Leonard says. "There were five or six a cappella groups in the states at that time, with the recording career we always aspired to. We were trying to break through on a more mainstream level. We were slowly trying to build ourselves for own music - not tied to coffee - and we had to be creative in how get to the public.
"We did not take a cookie-cutter path. We had to look for other ways to get to (the audiences). And so far, so good. We do about 100 shows a year around the world."
Keeping it fresh and having fun
Since Rockapella is better-known now that it was when it started, one of the challenges for the group is keeping the sound fresh.