Paul Dinello was born on November 28, 1962, in Oak Park, Illinois, where he was one of five siblings, consisting of one brother and three sisters. After completing his education at DePaul University, Dinello joined the renowned Second City Improvisation Troupe in Chicago, where he honed his skills and eventually met fellow comedians Stephen Colbert and Amy Sedaris. Following his stint with Second City, Dinello, along with Colbert, Sedaris, and Mitch Rouse, co-created the sketch comedy series Exit 57, which premiered on Comedy Central in 1995. The show, which aired for two seasons until 1996, garnered five CableAce nominations for outstanding writing, performing, and comedy series.
The trio's subsequent collaboration, Strangers with Candy, debuted on Comedy Central in 1999 and cleverly parodied after-school specials by presenting a problem that would be resolved within a single episode, but with a twist: the characters would learn the wrong lessons. The show enjoyed a successful three-season run and was later adapted into a feature film, Strangers with Candy (2005),which Dinello directed and co-starred in. Throughout his career, Dinello has appeared in numerous films, including Plump Fiction (1997) and Straight Talk (1992),and has also made his mark on the New York stage, particularly with The Talent Family's "Stitches".