Madigan first took a job in print journalism, working for the St. Louis-area Suburban Journals newspapers as well as the publications department of the Missouri Athletic Club. At the same time she performed stand-up during "open mic" nights at St. Louis area comedy clubs. She credits her father, Jack, with encouraging her to try a comedy career. Her growing popularity at these soon led to the offer of a paying job in stand-up from The Funny Bone, a nationwide chain of comedy clubs. With a thirty-week booking of guaranteed dates, Madigan gave up her jobs in Missouri. She cites Ron White, Richard Jeni and Lewis Black among her influences in those early comedy club days.