30 most shocking moments in late night history

NEW YORK - FEBRUARY 11: Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the Late Show with David Letterman Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images)
NEW YORK - FEBRUARY 11: Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the Late Show with David Letterman Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images) /
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9. Andy Dick invades Ivanka Trump’s personal space

You’ve seen Ivanka Trump in the news a lot lately supporting her father’s run for the White House, but in February 2007 people were talking about her for a much more uncomfortable reason. Trump had appeared as a guest on Jimmy Kimmel Live with comedian Andy Dick, and it quickly became apparent that Dick most likely wasn’t sober.

Dick demonstrated how he had lost all sense of boundaries by constantly touching Trump, which she obviously didn’t care for. It was annoying and uncomfortable for everyone watching, including Kimmel. Kimmel tried to tell Dick to stop, but the hints weren’t being recognized. Grabbing Trump yet again was the last straw for Dick, as Kimmel called over his security guards and helped them forcefully remove the comedian from the show.

It was never made clear whether Dick was inebriated, but Kimmel knew he was “out of it”. This wouldn’t be the last time Dick had caused trouble with his fellow comedians, however, as Jon Lovitz would assault him in a bar fight just mere months later. If only that moment had occurred on a late night television program, as that would surely be something high atop this list.

Next: 8. Harvey Pekar gets banished