I think Bruce Willis belongs on this list. But from the choices, I enjoyed Gene Wilder the most.
Leslie Jordan was hilarious whenever he appeared on Will & Grace.
Guest-acting awards were initiated in 1986. They first started off without separating the genders. In 1989 the current system we recognize took effect. Winners among the gentlemen guesting in comedy were:
1986: Roscoe Lee Brown, The Cosby Show (NBC)
1987: John Cleese, Cheers (NBC)
1989: Cleavon Little, Dear John (NBC)
1990: Jay Thomas, Murphy Brown (CBS)
1991: Jay Thomas, Murphy Brown (CBS)
1992: suspended (guests in that year’s awards were combined with series lead and supporting players)
1993: David Clennon, Dream On (HBO)
1994: Martin Sheen, Murphy Brown (CBS)
1995: Carl Reiner, Mad About You (NBC)
1996: Tim Conway, Coach (ABC)
1997: Mel Brooks, Mad About You (NBC)
1998: Mel Brooks, Mad About You (NBC)
1999: Mel Brooks, Mad About You (NBC)
2000: Bruce Willis, Friends (NBC)
2001: Derek Jacobi, Frasier (NBC)
2002: Anthony LaPaglia, Frasier (NBC)
2003: Gene Wilder, Will & Grace (NBC)
2004: John Turturro, Monk (USA Network)
2005: Bobby Cannavale, Will & Grace (NBC)
2006: Leslie Jordan, Will & Grace (NBC)
2007: Stanley Tucci, Monk (USA Network)
2008: Tim Conway, 30 Rock (NBC)
2009: Justin Timberlake, Saturday Night Live (NBC)
2010: Neil Patrick Harris, Glee (Fox)
2011: Justin Timberlake, Saturday Night Live (NBC)
I would go with Mel Brooks.
But just last night I saw Leslie Jordan on Will & Grace and the way they planned and wrote each of Beverly Leslie’s entrances was just genius. You just have to pay attention to the dialogue and you can almost guess when he’s going to show up.
The episode with the gay penguins was hilarious, Karen tells Grace that “Oh Grace, there’s no such thing as gay penguins” and of course! you hear the “Well Well Well if it isn’t Kaaaaren Waaaaalker” and he shows up in a tux looking like the gay penguin that he is.
Leslie Jordan was insanely perfect in this role, his delivery and physical comedy was amazing, a couple of weeks ago I saw him falling down from a bar, he also got pushed by Jack when he tried to be JLo’s backup dancer and Jordan just went for it.
It was an extremely deserved and overdue miracle when he not only got nominated but actually won for this show.