1.
Kanye West Interrupts Taylor Swift’s VMAs Acceptance Speech
Photo: YouTube screenshot
Aired: Sept. 13, 2009
Taylor Swift was shocked when she won her first MTV Video Music Award for Best Female Video — and she was even more shocked when Kanye West took to the stage and grabbed the microphone from her during her acceptance speech to declare that “Beyoncé had one of the best videos of all time.” The audience, understandably, erupted into boos, and even Queen B — who later invited Swift to finish her speech during one of her own wins — looked like she wanted to shrink away from Kanye’s outburst. —Vlada Gelman
2.
Ashlee Simpson Lip-Syncs on SNL
Photo: YouTube screenshot
Aired: Oct. 23, 2004
In an episode of Saturday Night Live hosted by Jude Law, Simpson first performed her single “Pieces of Me” without issue. But when it came time for her planned second song, “Autobiography,” Simpson’s vocals for “Pieces of Me” bizarrely began playing again before she’d even lifted the microphone to sing. What followed was an awkward minute in which Simpson did an uneasy dance, shrugged helplessly and exited the stage, leaving her band to play until a commercial break arrived. At the end of the episode, Simpson said her band had started to play the wrong song, confusing her; it later emerged that Simpson had lost her voice due to acid reflux complications, prompting her to lip-sync for her SNL performances. —Rebecca Iannucci
3.
Ron Artest Fights a Fan in ‘The Malice at the Palace’
Photo: Courtesy of Netflix
Aired: Nov. 19, 2004
What began as a typical NBA game became a dark day in basketball history when Pacers player Ron Artest got into a fight on the court that spilled over into the stands after a fan hit Artest with a drink. Artest chased the fan, with his teammates joining in and throwing punches, resulting in a wildly chaotic melee. The NBA called the incident “shocking, repulsive, and inexcusable,” and any viewer watching live would add another word: unforgettable. —Dave Nemetz
4.
Kanye West Calls Out President Bush During Hurricane Katrina Telethon
Photo: NBC screenshot
Aired: Sept. 2, 2005
We will never forget the surreal moment Kanye West went off script during NBC’s telethon to raise funds for Hurricane Katrina survivors and accused the president of being racist. “George Bush doesn’t care about Black people,” the Grammy-winning artist said after an impassioned rant criticizing FEMA’s delayed response, among other things. A stunned Mike Myers did a double take, and frantic producers quickly cut to Chris Tucker, who also looked taken aback. West has since apologized for the outburst, and Bush — who was Commander-in-Chief during 9/11 and the Iraq War — said it was the worst moment of his presidency. —Keisha Hatchett
5.
Jon Stewart Calls Tucker Carlson a ‘D–k’ on Crossfire
Photo: YouTube screenshot
Aired: Oct. 14, 2004
The then-host of The Daily Show appeared on the live CNN talk show Crossfire to promote his book “America: The Book,” but soon found himself pleading with hosts Tucker Carlson and Paul Begala to stop fueling partisan discord through political theater, particularly in an election year. The animosity, especially between Stewart and Carlson, escalated throughout the multi-segment appearance, until Carlson remarked that the comedian was funnier on his Comedy Central series. Just before the broadcast went to commercial, Stewart retorted, “You’re as much of a d–k on your show as you are on any show.” —Kimberly Roots