The Bizarre Details Behind The Time SNL’s Darrell Hammond Spent Four Days In Jail After A Cocaine Bust

Darrell Hammond has always stuck me as a fairly conservative person, although to be honest, we are so used to seeing him impersonating other people that it’s rare for us to actually see him when he’s not in some character. A couple of days ago, however, while I was trying to find out how Bill Clinton felt about Hammond’s impersonation of him (Clinton didn’t like Phil Hartman’s impersonation), I fell into a rabbit hole of Hammond’s life and ended up finding out more than I had bargained for.

The truth is, Hammond — the longest serving member of SNL cast ever, and the recently hired announcer on the show — has had a troubled and dark past. He was brutally abused by his mother as a child, has been diagnosed with bipolar disorder, schizophrenia, and borderline personality disorder, and has been in and out of rehab for much of his life for cocaine and alcohol addiction.

Yes, this Darrell Hammond:

But there’s one story about Darrell Hammond that stands above the rest, and it’s a story — as far as I can tell — that he’s only ever told three times: on two separate occasions on Loveline with Adam Carolla and Dr. Drew (in 1998 and 2004) and once on Opie and Anthony, in 2012.

It goes like this: Sometime around 1989 or 1990, Hammond was working as a stand-up performer on a cruise ship, which was docked in the Bahamas. One night on the ship, he drank something like 16 shots of golden rum. At that point, he was so drunk that, according to Hammond, it was as though he were living in an alternate reality in which he was convinced he was going to play baseball for the New York Yankees.

Under that level of intoxication, he found himself in a bathroom, where a guy who was handing out very small samples of cocaine walked into the stall with Hammond (who was exposed at the time), and said, “I think you should take this with you.” It was a dollar bill with an amount of coke on it so small that it couldn’t even be measured. Hammond took it so the guy would leave his stall, but when he walked out of the bathroom, five cops were waiting for him.

Basically, according to the DEA, Hammond had been entrapped as part of a scheme employed by cops in the Bahamas on 12 cruise ships a night. (At least, that’s what he said in 1998. Hammond did not mention being set up in the 2004 account of the story, only that he’d been nabbed.)

In both accounts, however, he did end up in a “horrifying” Jamaican jail cell with other people’s feces all over the floor, where people were given a trial, fined, and “if you don’t have the money, you will die in there.” Finally, on his fourth day of imprisonment, he was given that trial.

A barefoot man came to me on my fourth day, as I was approaching the trial [being held] in chains [walked] through the town square, and my father had flown in with all the cash he could get his hands on. And [the barefoot man] walks up to my Dad and says, ‘I’ll get your son off for $500 cash up front.’ My father tried to haggle with him, and offered him $300 upfront and another $200 if [Hammond] got off. The guy goes, ‘OH, OK. Sure!’ And he was bombed.

Basically, Hammond was told that if he got a “good” judge, he’d be sent away to prison (probably for 18 months). But that if he got a corrupt judge, he could throw a lot of money at him and get out. I guess he found a corrupt judge because his father ended up paying $3,000 and Hammond was released.

The experience, Hammond recalls, was a wake-up call for him. Being in a horrifying, unkempt Jamaican prison cell for four days brought him a lot of clarity, although not so much that he’d stay straight for the rest of his life (the year after the prison incident, he got married, and the year after that, he had the first of a few relapses, and a divorce, although he’d remarry the same woman in 2007 and divorce her AGAIN a few years later).

It’s a bizarre story, and according to Tina Fey, not a story he ever told until that first Loveline episode.

Source: Loveline Tapes and Last.FM