Midway between the 2004–2005 season, Hammond set the record for the longest consecutive tenure of any SNL cast member in the show's history. He also holds SNL records for most impressions by a single cast-member, and most times for saying the legendary catch-phrase "Live from New York, it's Saturday Night!" to start the show (beating out Dana Carvey). He is also the only cast member to have a "Best Of..." compilation special while still a castmember.
Principally an impressionist, he became famous for his impressions of Arnold Schwarzenegger, Ted Koppel, Bill O'Reilly, Regis Philbin, Jack Perkins, Dick Cheney, Colin Powell, Donald Rumsfeld, Dr. Phil, Jesse Jackson, Phil Donahue, Don Imus, Jay Leno, Bob Costas, Tim Russert, Dan Rather, Geraldo Rivera, Richard Dreyfuss, Tony Soprano, Rudolph Giuliani, Al Gore, and George W. Bush. Although he does many impressions, he is best known for his segments impersonating Sean Connery, Bill Clinton, Chris Matthews from "Hardball", and more recently Donald Trump. When veteran announcer Don Pardo is unavailable, Hammond fills in to introduce the cast, with a spot-on Pardo impersonation. In the film Epic Movie, he parodies Johnny Depp's role as Captain Jack Sparrow from Pirates of the Caribbean. On several occasions his fake moustaches seem to fall off, examples of this can be seen in the Ludacris episode as well as the Ian McKellen/Kylie Minogue episode (both of which were covered up by ad-libs referring to Hammond's mustache coming undone).
In the late 1980s, Hammond gained fame for his impersonations of Elmer Fudd and other Looney Tunes characters in the comedy single "Wappin'." The song was so popular with Dr. Demento listeners, it was included on the show's 20th Anniversary compilation.
Hammond is a frequent guest on The Howard Stern Show. He has also guest starred in episodes of Law & Order: Special Victims Unit and Law & Order: Criminal Intent. He had his own stand-up comedy special on Comedy Central: "Comedy Central Presents Darrell Hammond." Hammond can frequently be seen at The Comedy Cellar in New York City.
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