Although he may have been expected to vault to the ranks of leading men, the handsome Elwes continued to accept supporting roles that demonstrated his versatility. He proved effective as the second-in-command to Matthew Broderick in the Civil War epic "Glory" (1989), and exhibited a flair for broad comedy as Charlie Sheen's rival in "Hot Shots!" (1991), the Jim Abrahams "Top Gun" parody. Although his portrayal of Lord Holmwood got lost behind the grand visuals of Francis Ford Coppola's "Bram Stoker's Dracula" (1992), he managed to rebound with a dead-on parody of Errol Flynn (by way of Kevin Costner) as a slightly dim denizen of Sherwood Forest in Mel Brooks' zany spoof "Robin Hood: Men In Tights" (1993). In the video hit "The Crush" (also 1993), Elwes was cast more for his looks than his acting, portraying the clueless journalist who finds himself the object of affection of his landlord's unhinged teenaged daughter (Alicia Silverstone). His screen characterizations took on a darker shading for the first time in the remake of "Rudyard Kipling's The Jungle Book" (1994), in which he played a corrupt British officer whose greed and arrogance spoiled the jungle boy's idyllic existence. He followed in the same vein as the corporate-sponsored rival to Bill Paxton in "Twister" (1996) and as a detective in the thriller "Kiss the Girls" (1997). The actor also provided a fine voice characterization for the blind hero of the animated "Quest for Camelot" (1998) before delivering a well-received turn as a slightly fey John Houseman in Tim Robbins' period drama "Cradle Will Rock" (1999). He subsequently lent his swashbuckling appeal to the supporting role of German cinematographer Fritz Arno Wagner in "Shadow of the Vampire" (2000), the fictionalized look at the behind-the-scenes making of F W Murnau's 1922 masterpiece "Nosferatu".

Although the stage-trained actor was once quoted as saying he preferred not to work in television, he ventured onto the small screen with a memorable guest appearance in a 1996 episode of the hit NBC sitcom "Seinfeld". Thereafter, Elwes was cast as a whistle-blower out to expose the US military's profligate spending in the based-on-fact satire "The Pentagon Wars" (HBO, 1998) and then segued to portraying Apollo 11 astronaut Michael Collins in the Tom Hanks-produced HBO miniseries "From the Earth to the Moon" (also 1998). Shortly thereafter, he also starred as a British military officer who befriends an IRA terrorist in the Showtime telefilm "The Informant".