Lost in Yonkers is certainly a comic play in many ways, and has many funny moments. It even ends in a relatively happier place than it begins. However, it includes many elements that prevent it from being a full-blown comedy. The play marked Simon's maturation as a writer, his transition into writing more serious fare in the late 80s and 90s. However, before this, Simon was known as a comic master, a prolific writer of comedic plays, films, and television.
Before becoming a playwright, Neil Simon wrote for the television comics Phil Silvers and Sid Caesar. While working these jobs, he honed his comic chops and learned to write a well-oiled joke. These skills would serve him in his early theatrical hits. Barefoot in the Park was his first breakthrough in 1963 and is still heralded as one of the most beloved American romantic comedies. It follows two newlyweds living in Greenwich Village and encountering some eccentric companions along the way. A film version starred Robert Redford and Jane Fonda. Simon's other big comedy was The Odd Couple in 1965, about a pair of unlikely roommates, divorcé men, one neurotic and the other outrageously sloppy. A film version starred Jack Lemmon and Walter Matthau. Both of these plays solidified Simon's reputation as a comic genius.
Simon's brand of comedy was never light or flimsy and was always derived from pathos and a more well-rounded human experience, even in his lighter fare. In Simon's obituary in The New York Times, Charles Isherwood wrote, "Agony is at the root of comedy, and for Mr. Simon it was the agony of an unhappy Depression-era childhood that inspired much of his finest work. And it was the agony of living in Los Angeles that drove his determination to break free from the grind of cranking out jokes for Jerry Lewis on television and make his own name." Indeed, Simon suffered from a highly unstable home life as a child, and his antidote as an artist was to find the joke in the difficult situation.
It seems that even Simon did not know how profoundly funny his work was until it came into contact with an audience. In an interview for NPR with Terry Gross, Simon said of The Odd Couple, "I thought I was writing, as I said, this grim comedy, until I gave it to Bob Fosse, a good friend of mine who lived in the same building, to read. And he says, this is the funniest play I've ever read. And I said, you don't find it dark? And he said, no, not at all. So the author is not always sure about what impression he's going to leave when he writes this thing."
