By the end of 1993, The State had secured a deal with MTV for six episodes of a sketch comedy series aptly named "The State", Ravaged by reviewers when it debuted in January 1994, the series nevertheless won decent ratings and a fiercely loyal fan base and stayed on the air for three seasons. Disagreements with MTV and a desire to head to a regular network led to the 1995 demise of the series. A deal with CBS would have them creating holiday specials with the option to become a regular program running against NBC's "Saturday Night Live", but the poor ratings of the CBS-aired "The State's 43rd Annual Halloween Special" (1995) severed that relationship.
Though his boyish good looks could have translated to more mainstream roles like his guest work on the ABC series "NYPD Blue" and "Spin City" in 1994 and 1998, respectively, Black preferred to stay on the edge. Following the demise of The State's TV career, he reteamed with fellow members of the troupe on other edgy projects including the weekly comedy staging of "Stella" at Fez in New York City. "Viva Variety" (Comedy Central, 1997-98), a spin-off based on a sketch aired on "The State" would reunite Black with troupe members Thomas Lennon and Kerri Kenney. In this satire of odd European variety shows, he played Johnny Blue Jeans, a wannabe American teen heartthrob to their bickering divorced couple. Beginning in 1999, Black would pop up in television commercials that, while not featuring him physically, certainly embodied his comic sense as well as employing his vocal talents. As the Pets.com sock puppet, he not only won over millions of viewers, but spawned a line of branded merchandise.
Fall 2000 marked the actor's first network regular series role, playing Phil, an exceptionally strange resident of a small town who works at and lives in the local bowling alley on the appropriately quirky comedy series "Ed". When his place of business/residence is acquired by the titular New York City lawyer who has returned home, Phil masterminds a plan to increase bowling business by offering Ed's legal services on site. Black excelled in his portrayal of the peculiar and unpredictable character. Having made his feature debut in the 1997-lensed "Big Helium Dog", Black would return to the big screen in the comedy "Wet Hot American Summer" (lensed 2000), a production that once again reunited him with various members of "The State."