Van Zandt, whose zany style and wacky onstage antics made him a memorable member of the E Street Band, embarked on a solo career beginning with the 1982 debut album of Little Steven and the Disciples of Soul entitled "Men Without Women". He left the E Street Band to focus on his solo work in 1984, at the height of Springsteen's "Born in the U.S.A." success. The musician's active political conscience marked his solo work, and among his most notable efforts was 1985's "Sun City", a various artists project bringing together both rock and rap superstars in the interest of combating South African apartheid, a hot button issue of the time. He followed up with a series of acclaimed lower profile albums but after the 1989 Europe-only release of "Revolution", Van Zandt took a career break, emerging from his virtual retirement to perform his original holiday hit "All Alone on Christmas" with Darlene Love for the "Home Alone 2: Lost in New York" soundtrack. Around this time, his Southside Johnny and the Asbury Jukes hit "I Don't Want to Go Home" served as an appropriate theme song for the Jersey Shore set sitcom "Down the Shore" (Fox, 1992-1993).

In 1999, the performer ended his downtime in a big way, embarking on the Bruce Springsteen and the E Street Band reunion tour while starring on "The Sopranos". Joining the band's sold-out jaunt was an exciting but expected move for the musician, but his entry into acting was certainly a surprise. He was invited to audition by "The Sopranos" creator David Chase, a longtime fan of Van Zandt's solo as well as collaborative work who saw promise in the magnetic onstage performer. Certainly Van Zandt's dark-hair, olive-skin and distinctly prominent features would suit a character player on the series, and after reading for the part of Tony Soprano, the budding actor so impressed Chase with his ability (and his concerns about taking a job away from a deserving actor) that the creator added the part of Silvio Dante just to have him on board. Donning a black bouffant wig that completely transformed his look from gypsy rock and roller to no-nonsense wise guy, an unrecognizable Van Zandt made his acting debut as operator of the central Bada Bing strip club and a ruthless and loyal right hand man to boss Tony Soprano (James Gandolfini). Fiercely protective of both his crime family and his nuclear family, Dante was an interesting character, known to calculatingly make deals and bash heads, but easily lose his cool at his school-age daughter's soccer games. The actor gave a consistently strong performance in the role, portraying the character sympathetically while effectively putting across the shocking brutality, and managed to balance this taxing work with a high-profile concert tour and the release of his first musical solo endeavor in a decade, the critically lauded hard-rocking album "Born Again Savage" (1999). Working for a mob boss and The Boss, two of the most successful and revered living New Jersey exports, Van Zandt rode the success of "The Sopranos" and the Springsteen tour straight through to the next millennium, with an acclaimed second season and second leg respectively in 2000.