Over the years, SNL has only had two Letterman impersonators of note.
"Late Night" premiered on February 1, 1982. On Feb. 20, SNL got what may be its first jab at Dave in a "Bizarro World" sketch (everything is opposite... Tom Snyder is rewarded by having his show canceled for Dave's). Five months later (July 8), Joe Piscopo made his first and only appearance on the show. And when SNL returned for season eight, Piscopo lampooned "Late Night" on its season premiere (9/25/82, with host Chevy Chase and musical guest, Queen). This sketch is not online, but it's a spot-on take; the audience even seems startled at how good it is.
Piscopo returned to play Dave on SNL on the season finale (5/14/83, Ed Koch/Kevin Rowland & Dexy's Midnight Runners) during a pretty weak episode (it came a week after the classic show hosted by Stevie Wonder; maybe the writers were wiped out).
Piscopo trotted out the impression on SNL just once more, during the classic episode hosted by Don Rickles (1/21/84, with musical guest Billy Idol) in a brief promo for (the real) Dave's 2nd Anniversary Show (which would air the following week in SNL's time slot). Oddly enough, this sketch is also online. Perhaps the impression wasn't done more frequently due to SNL not wanting to mock a show they likely were fans of.
Piscopo would later host two specials (and he portrayed Dave in at least one), which seem like pilots for a variety show. Neither one was picked up, but today Piscopo still trots out his aged impression of Letterman, complete with wacky, high-pitched laugh. He actually performed it during his lone appearance on the CBS "Late Show with David Letterman" during "Impressionist's Week" (5/3/07). Dave seems to mildly enjoy it here. He did NOT enjoy Piscopo imitating him (to his face) on "The Tonight Show Starring Johnny Carson" (10/23/87 -- Johnny's 62nd birthday) even though Joe seems like he's trying to be incredibly good-natured and friendly about it.
Fast-forwarding, Norm Macdonald -- an incredible standup and huge fan of Dave's -- played Letterman on three occasions: Kevin Spacey/Beck (1/11/97), Alec Baldwin/Tina Turner (2/22/97) and Jon Lovitz/Jane's Addiction (11/8/97). I'm always struck by how accurate this impression is of mid-'90s, laissez faire Dave, and yet how different it is from the Piscopo take (which was totally accurate for the early '80s).
Macdonald's version comes from the years between when Dave was beating Leno's show and living the dream in what Rolling Stone magazine called "Dave's Funhouse" (1993-95), and the years when he became an elder statesman of TV and started winning Emmys (1997-02). This laissez faire era (1995-97) roughly coincides with when Les Moonves came to CBS (whom Dave did not care for), the network was falling further behind NBC due to the rise of "Seinfeld," "Friends" and "ER," CBS was bought and sold a few times, and Dave had to send some key production staff (such as Jude Brennan and Peter Lasally) to produce "The Late Late Show with Tom Snyder." Within the show, many key players left entirely around this time, too: announcer Bill Wendell and director Hal Gurnee both retired. Confidante and producer Robert Morton was fired for trying to move the show to ABC (and Head Writer Rob Burnett had to be promoted to take his place). The end of this period seems to coincide with the hiring of Justin & Eric Stangel as head writers.
Back to SNL, Norm actually performed his impersonation for Dave after some gentle mocking on a "Late Show" in the late 1990s. This was during the period when he was frequently discussing his problems at SNL on the show with Dave. Several times, Norm says he only enjoyed "Weekend Update" because he was no-good in sketches (certainly not true, as evidenced by the Letterman impression and all the "Stan Hooper" skteches, for starters).
SNL has only imitated Letterman once more (3/9/02) with host Jon Stewart. This was at a time when it seemed like a very real possibility that Dave would jump to ABC, displacing "Nightline," and Stewart would finally be given a shot at 11:30 on a network.
None of that happened, of course: Dave stayed put and later appeared with "Nightline" host Ted Koppel for an interview (out of respect). Stewart was just finding his talents for tearing into politicians at this point, six months after 9/11, and obviously would guide "The Daily Show" to big success over the next 13 years. On his lone SNL outing, Stewart played himself in a sketch alongside impressions of other late night hosts. Letterman is played by Jeff Richards, and it's weak: he looks and sounds more like "Evil Dave" from the Howard Stern show.
As a final shout-out (not actually on SNL) Seth Meyers recreated the original open for "Late Night" (which was used from 1982-86 or so) the night before Dave's last show.
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