Simpson’s 2004 Saturday Night Live performance went down in infamy. When the vocals for the wrong song started playing, Simpson did an awkward hoedown before walking off the stage.
Ashlee Simpson booed at the Orange Bowl
Simpson never quite recovered from the SNL performance. In 2005, the singer was booed after her performance at the Orange Bowl.
Katy Perry slips in cake on stage
During a 2008 performance of “I Kissed a Girl,” Perry dived into a giant cake, only to flail awkwardly and then slip on stage.
When Spears performed “Gimme More” at the 2007 Video Music Awards, it was supposed to be a comeback, but it was painfully awkward.
Janet Jackson’s Super Bowl wardrobe malfunction
In 2004, Janet Jackson and Justin Timberlake’s Super Bowl performance became infamous when a “wardrobe malfunction” left Jackson exposed on live television.
Michelle Williams falls during 106 & Park Performance
During a 2004 106 & Park performance, Michelle Williams fell on stage—and her Destiny’s Child bandmates continued with the performance seamlessly.
Katy Perry pretends to play the flute
It’s one thing to get caught lip syncing, but to get caught pretending to play an instrument is next level. Perry was caught pretending to play the flute during a cover of “Big Pimpin'” and her reaction was classic.
Pink falls off stage
Pink made headlines when she fell off stage and injured herself during a show in Germany in 2010.