Having reached a whole new audience thanks to the success of "Dead Skunk", Wainwright saw his profile rise, leading to a 1974-75 recurring role as a singing surgeon on "M*A*S*H" (CBS). Wainwright proved not only a charismatic and highly watchable presence, he showed that he did indeed have some acting talents to go along with his musical ones. Keeping the focus on his music, Wainwright nevertheless subsequently ended up in the occasional screen role, appearing in Hal Ashby's "The Slugger's Wife" in 1985. That same year he garnered his first Grammy nomination for his album "I'm Alright". In 1986 the honor was repeated, this time for the album "More Love Songs". Staying just below the radar despite critical praise and a strong cult following, Wainwright was persuaded by his sister Teddy to take a job as a musical commentator for National Public Radio (NPR). His heartfelt and often snarky take on current events for NPR was collected and released in 1999 as the album "Social Studies".
2000 saw Wainwright return to the big screen, his running musical commentary in the film "28 Days" somewhat reminiscent of Jonathan Richman's explanatory chorus throughout "There's Something About Mary" (1999), though it was neither as consistent nor distracting. Gray-haired, bespectacled and decidedly dad-like, Wainwright no longer wore the physical cues of a challenging troubadour, but while he was settling down with a regular role as a sweetly off-kilter father on the college-set Fox sitcom "Undeclared" (cast thanks to producer Judd Apatow's longtime love of his music), his album "The Last Man on Earth" was released, inspiring many critics to deem this sitcom actor's creative voice as vital as it was thirty years prior.