[4] Hammond's father, dealing with his own psychological problems resulting from his military service during World War II, often drank heavily and acted out violently.
[6] After completing college, Hammond moved to New York City where he worked as a waiter, studied at HB Studio, played roles in theater productions, and performed one set at a comedy club at age 26.
Hammond then returned to Florida where he was a radio DJ at BJ 105 FM, telling Howard Stern in 2002, "First I tried to be a jock, which I really sucked at," followed by being a voiceover artist in the Orlando area.
After an exclusive audition for creator and executive producer Lorne Michaels, Hammond was brought on board as a cast member and performed for 14 seasons.
[8] He previously held the record for the longest consecutive tenure of any SNL cast member in the show's history, until he was surpassed by Kenan Thompson in 2017.
[citation needed] He is best known on the show for not only his impersonations of Bill Clinton, but also Al Gore, Donald Trump, John McCain, Regis Philbin, Dick Cheney, Chris Matthews, Phil Donahue, Phil McGraw, Ted Koppel, John Travolta, Jesse Jackson, Geraldo Rivera, Dan Rather, and Sean Connery, in the recurring "Celebrity Jeopardy!"
In the summer of 2007, Hammond made his Broadway theatre debut, playing the role of Vice Principal Douglas Panch in The 25th Annual Putnam County Spelling Bee.
[12] Beginning in May 2015, Hammond began playing the role of fast-food mascot Colonel Sanders in an ad campaign for KFC, until Norm Macdonald replaced him on August 17, 2015.
[13] Since returning to Los Angeles in 2017, Hammond has appeared in episodes of Criminal Minds, At Home with Amy Sedaris, and a Friday Night Lights spoof series on sports website The Kicker.
[20] The incident helped him come to terms with what he and the doctor who treated him realized was his fundamental concern, the posttraumatic stress disorder stemming from his abusive childhood.
[5] Just prior to his 2000 appearance as Al Gore in a sketch parodying that year's first presidential debate, he had a panic attack due to forgetting his lines.
[16] In 2015 he adapted it into a one-man play starring himself, directed by Christopher Ashley, which debuted in San Diego, California, at La Jolla Playhouse to positive reviews.
The director has expressed plans for a Broadway residency, although Hammond stated he would prefer an actor to play him instead, as he found the tour so stressful he had to be hospitalized twice during the Los Angeles run.
When Alec Baldwin replaced him, he fell into a deep depression and was prescribed Antabuse and a beta blocker to prevent a relapse of his addiction problems.
According to Hammond, the United States Drug Enforcement Administration later told him that the episode had been a setup, and that local authorities regularly entrap American tourists;[21] he spent a weekend in jail.