Higgins was born on August 13, 1963, in Des Moines, Iowa, to Marian (née Coppola) and Harold Higgins, who managed the custodial operations in West Des Moines schools. He was one of five children, including his brothers David and Alan.
Higgins formed the comedy troupe "Don't Quit Your Day Job," with brothers David and Alan and friend Dave "Gruber" Allen. Country music star David Allen Coe was also seen playing Iowa back woods clubs during this time period, causing much confusion among fans and promoters and leading to some embarrassing double bookings of Coe and Gruber or of Coe and Higgins. The comedy troupe did make it through these times with Dave Allen at the helm. They performed at notable places in Iowa including the Hotel Kirkwood, Corky's, and the Spaghetti Works.
They eventually moved to California, where they started performing in Los Angeles and soon got their big break on the Comedy Central sketch comedy series The Higgins Boys and Gruber. Following a very lean year after their third year performing the group was suddenly relegated to selling donated "merch" at yard sales in the Mississippi back woods. These forays into sales usually netted the group lunch money or at least
Vienna sausage money.
In 1989, Higgins performed at The Vic Theatre in Chicago for HBO's One Night Stand television series, along with his brother Dave, and Gruber. Alongside Nick Bakay, Higgins performed in 1993 at the Girly Magazine Party show at Theatre/Theater in Hollywood, Los Angeles. They played "a sleazoid male chauvinist comedy duo who exchange off-color ethnic jokes and prance around in suits and ties like Steve Martin on PCP". His brother, Dave, performed in the show and in a separate act. Higgins was praised for his ability of knowing "when to go over the top and when to rein it in", and how he was able to be "acutely tuned in to the comings and goings around them and know how to play off each other". Soon after, Higgins went on to become a writer for the short-lived MTV programs Trashed and The Jon Stewart Show.

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