Molaskey was born and raised in rural Connecticut. When her father died just as she was about to graduate from high school, her hopes of an ivy-covered college degree died with him. Instead, because of her love for the original cast albums of Broadway musicals she'd never seen, she went to New York "with nothing but $150 and my collection of LPs."
After one semester at the American Academy of Dramatic Arts, Molaskey's roommate (who was from St. Louis) suggested that she audition for the Muny. Cast in the 1978 singing ensemble, she enjoyed a summer of firsts. "It was absolutely the first job I ever had," Molaskey recalls. "Flying to St. Louis was the first time I was ever on an airplane. And I got my Equity card. My first show was Oklahoma! I still remember walking out on the stage in the July heat wearing a wool outfit from the original Oklahoma! company and thinking I was going to die. But it turned out to be a fun, fun summer. I had a ball."
The Oklahoma! cast featured crusty old St. Louis favorite Mary Wickes as Aunt Eller. "She took a shine to me," Molaskey says. "I don't know why, except that I think she admired people who wanted to work hard, and I always enjoyed that. She knew I was in school in New York, and she said, 'I'm coming to Broadway in a revival of Oklahoma! and I'm going to talk to the director about you.' I didn't think all that much about it, but six months later I got a call. There were a thousand people at the audition, and I went to the head of the line and said, 'Mary Wickes recommended me,' and I got the job, which was a life-saver."
The production, which re-created Agnes de Mille's legendary choreography, toured for six months before opening at Broadway's Palace Theater. During previews, de Mille pulled the neophyte aside and brusquely asked, "Who hired you?" To which Molaskey replied, "You did, Miss de Mille." Looking back on her first New York show, Molaskey now says, "I had a lot of spunk, but not a lot of technique. Spunk sometimes can make you stand out from the crowd. But after six months they start asking, 'What the heck happened here?'"
What happened was that the technique began to develop and has continued to deepen. She has performed in such long-running New York shows as Cats and Les Misérables and has debuted new songs by the likes of Stephen Sondheim, Jason Robert Brown and Adam Guettel. Nine years ago, while appearing in a Johnny Mercer revue on Broadway, she met (and soon married) jazz musician John Pizzarelli. "It's the most life-changing thing that ever happened to me," Molaskey says. "He's the most wonderful person and my best friend. But I don't want to talk too much about him, because I'm leery of all those people who claim to be the greatest couple, and then three months later...."
The only drawback to her current career is that the birth of their daughter keeps Molaskey away from theater. "I miss terribly being in the company of actors and directors," she says. "There's nothing in the whole world like coming together to make a play happen. But I'm only going to be a mom once, and I want to make sure I do it correctly."
Hence the transition to cabaret, where she brings a new kind of vitality to theater songs: "My husband and I both try to show that Broadway songs can exist alone. They're like little plays." And next week when she sets Oklahoma!'s "I Cain't Say No" on its ear with a refreshing new spin, it's a safe bet that for just a moment Molaskey will be transported back to Mary Wickes and the Muny and a road that continues to surprise.