Ashlee Simpson and other SNL gaffes we’ll never forget

When you think of Ashlee Simpson, there’s probably only one image that comes to mind: her lip-syncing snafu on SNL, in which she went to perform her second song of the night, only for the playback to trigger her first song, “Pieces of Me”. She had been caught going full Milli Vanilli. And to get herself out of the situation, Simpson basically la-la’d her way off stage while doing a jig, leaving her band behind to “play”. Twenty years after the incident, Simpson is remembering the moment as a life lesson. But this may not be the case for others who also made some serious bonehead moves on SNL…

It’s extremely rare for musical guests on SNL to go through gaffes of Ashlee Simpson’s magnitude: musicians like Elvis Costello would instead raise intentional hell by playing whatever song he wanted, while Sinead O’Connor used her moment to send a message. More often than not, it’s the guest hosts who goof, leading to humiliation and sometimes lifetime bans.

Let’s start with Martin Lawrence, who led off his 1991 stint as host with a monologue that went completely off script, riffing on feminine hygiene and John and Lorena Bobbitt, the latter of whom had cut off her husband’s penis (the subject of many-a Weekend Update segment). Yes, Martin Lawrence has a permanent ban. Another host saved his gaffe for later on in the show. In 2003, Adrien Brody tried to pay homage to the Jamaican roots of musical guest Sean Paul, turning up in full rastafarian mode, complete with dreadlocks and a faux accent that was of course immediately deemed to be inappropriate and racist. He, too, would be banned.

Sometimes the presence of a host alone can be enough for controversy, as was the case with Andrew Dice Clay, whose 1990 gig prompted SNL cast members like Nora Dunn to refuse to work that week. Clay would go on with the show but numerous protests were spawned due to the comedian’s act containing derogatory remarks about women. Steven Seagal also caused trouble behind the scenes, proving a true pain in the ass to the cast. Lorne Michaels would go on to take the understandable stance that Seagal was the worst SNL host ever.

But gaffes have done plenty of SNL cast members dirty, too. In 1981, player Charles Rocket erred by dropping the f-bomb during the closing monologue; he would be fired from the show after just one season. In 1997, Weekend Update host Norm Macdonald slipped after making a strange noise, saying, “What the f*ck was that?” Knowing he goofed immediately, Macdonald joked that it would be his “farewell performance”…he would be fired later that season (although part of that had to do with slamming NBC president Don Ohlmer’s buddy O.J. Simpson).

On her own SNL incident, Ashlee Simpson – appearing on Broad Ideas with Rachel Bilson & Olivia Allen (via People) – said of the moment, “It taught me humility, it taught me so much about myself and my own personal strength,” adding that it gave her resiliency in terms of dusting off her boots. As for why she opted not to sing at all, she cites a case of acid reflux, leaving her without proper vocals. Steven Seagal could not make the same claim…

But these are only a fraction of those who suffered embarrassing incidents on SNL. Which guest or host do you think had the most damaging on-air flub? Give us your picks below!