Saturday Night Live
At 32 years old, Hammond moved back to New York to make one last attempt at being a stand-up comedian. After seven years and two failed Saturday Night Live auditions, he was spotted in 1995 by an SNL producer while doing a Bill Clinton impression - shortly after Phil Hartman, who had portrayed Clinton, left the show. After an exclusive audition for creator and executive producer Lorne Michaels, Hammond was brought on board as a cast member and remained a cast member for 14 seasons. Before Kenan Thompson overtook him in 2017, he held the record as the longest-tenured cast member in SNL's history.
He also holds SNL records for the second most impressions by a single cast member (107, as of the Zac Efron/Yeah Yeah Yeahs episode), exceeded only by Thompson, and also for being the cast member who has uttered the iconic catchphrase "Live from New York, it's Saturday Night!" to start the show the highest number of times (76, beating out Dana Carvey).
He is best known on the show not only for his impersonations of Bill Clinton, but also of Al Gore, Donald Trump, John McCain, Regis Philbin, Dick Cheney, Chris Matthews, Rodney Dangerfield, Richard Dreyfuss, Phil Donahue, Phil McGraw, Ted Koppel, John Travolta, Jesse Jackson, Geraldo Rivera, Dan Rather, and Sean Connery, in the recurring "Celebrity Jeopardy!" skits. No one on SNL has done any one impression more than Hammond's Clinton, having impersonated him in 87 sketches over 14 years in the cast and in numerous additional cameos. Hammond also impersonated SNL announcer Don Pardo, filling in for Pardo on occasions when the announcer was unavailable.
Hammond initially planned to leave Saturday Night Live, after the conclusion of season 31, after 11 years, but many people at SNL, including his then-manager Bernie Brillstein, advised him to stay on. He describes his last three seasons as a difficult period, as all the writers who knew how to write for him had left by the start of his 12th season, and he wasn't assigned to portray any members of the incoming Obama administration.
After the end of SNL's 34th year, Hammond retired from the show after a record-breaking 14 years as a repertory player. Hammond was the last SNL cast member from the 1990s to leave the show.
In 2014, Hammond took over the announcer role on SNL starting with the 40th-season premiere, replacing Pardo, who had died a month prior. He was told by executive producer Lorne Michaels not to directly impersonate Pardo, so Hammond ended up using his own voice for the announcement gig. Since he began as announcer, he has also reprised his Clinton and Trump impersonations in several skits.
The following season Hammond reappeared on the show, doing his impression of Trump just as the real Trump began performing well in the Republican primaries. Hammond moved back to New York in 2016 after Trump won the nomination, expecting to be appearing on a weekly basis during the election. However, SNL producer Lorne Michaels decided instead to go with Alec Baldwin's impression, believing that it more effectively captured the contemporary Trump.
