Tolan was born in Scituate, Massachusetts, where he was a perennial favorite in the high school's dramatic productions. Before leaving to pursue a career in Hollywood, Tolan founded a theater group called YPST (Young People's Summer Theatre). The group performed Broadway musicals and rehearsed at a local church. Within three years, the group became so popular that a second production had to be added to accommodate the ever-increasing enrollment. Tolan attended the University of Massachusetts Amherst for four years before dropping out to directly pursue theater. From college Tolan went to Minneapolis' Brave New Workshop (founded by improv great Dudley Riggs) at the suggestion of UMass employee Jim MacRostie, who had appeared at the Twin Cities institution during its early years. Riggs offered Tolan a job over the phone, but when Tolan arrived in Minneapolis several months later, he discovered that the job was that of janitor at the theater. Within a year, Tolan became the musical Director for the theater's touring company, and after that graduated to appearing as a member of the main stage cast. In the mid 80's, Tolan moved to New York City, where he and fellow writer-performer Linda Wallem formed a double act called Wallem & Tolan and began performing on the cabaret circuit in New York City at such venues as Don't Tell Mama, Eighty-Eights and Broadway Baby. Wallem and Tolan were known for their Sketch work and for musical material (written by Tolan) that became the cornerstone of their act. After an extended run at the Manhattan Punch Line Theater, the act was mounted Off-Broadway at the Theater at St. Peter's Church in 1989. Titled "Laughing Matters," the show was produced by Sanford Fisher and Zev Guber and directed by Broadway veteran Martin Charnin. For his work in the show, Tolan was named Outstanding Lyricist of a Broadway or Off-Broadway Show by the Burns Mantle Theater Yearbook 1988-1989 Best Plays.