Several years after appearing in a string of films based on "Saturday Night Live" sketches including "Coneheads" and "Wayne's World 2" (both 1993), Meadows was offered his own chance at features, and the 2000 release "The Ladies' Man" gave the eponymous hero Leon Phelps the opportunity to bring his inane romantic advice to the big screen. That same year he left "SNL" to join NBC's primetime line-up as a regular cast member on "The Michael Richards Show". Here Meadows played a private detective trying to overcome his Peeping Tom tendencies, one of the workmates of P.I. Vic Nardozza (Richards).
Meadows' additional credits include a 1996 stint at the Kennedy Center as a featured performer in the Second City production "Truth, Justice, and the American Way". He was also featured in a 1999 episode of Comedy Central's odd series "Strangers With Candy" and lent his voice to the animated holiday special "Olive, the Other Reindeer" (Fox, 1999). A supporter of the Free Tibet movement, the actor-comedian was featured in PSAs for the organization that drew parallels between the present-day Tibetan struggle for civil rights and the similar African-American movement of the 1960s.