Judith Light's Scandalous 1995 Appearance On Jay Leno Shook Up Late-Night TV

"Who's the Boss?" star Judith Light once had a salacious late-night appearance that sent viewers into a tailspin and had people questioning Jay Leno's behavior. Light was a guest on "The Tonight Show with Jay Leno" in April 1995 alongside David Spade and Chris Farley. While interviewing Light about her new movie, Leno took an odd line of questioning, saying he paused her film "Women in Prison" on a shower scene. "I'm surprised you didn't tell everybody that I used to be a p***titute ... I mean in 'One Life to Live,'" the actor jokingly responded.

Light decided to stay with the line of questioning and mentioned that her new character had spicy scenes. "I am naked a bit in this movie," she told Leno. "I happen to be wearing the outfit that I wore," she then informed him. The "Ugly Betty" actor wore a black dress that could be easily taken off to show her undergarments. Light beckoned Leno to come from behind the desk and help demonstrate. He unbuttoned her gown, and she stood there in a lacy black nightie. "Can you cut to commercial now?" Light asked, but Leno continued the segment. Meanwhile, Farley went into hound dog mode and started enthusiastically jumping around as Light's figure was on display. At one point, Leno asked what Farley thought, and the "Tommy Boy" star kissed Light's hand.

After his questionable behavior while she showed off the tearaway dress, it would not be surprising if Light became one of the celebs who can't stand Leno. Later, the segment was shared online and fans voiced their disapproval. "Leno being a old hazz creeper," one YouTuber commented. "It's not only Farley that makes this interview awkward, Jays questions are also bizarre," a Redditor wrote. Leno's strange questioning also caused an uncomfortable moment with Kanye West.

Another scandalous moment on "The Tonight Show with Jay Leno" happened when Kanye West came on the show to publicly apologize after he infamously stole the microphone from Taylor Swift at the MTV VMAs. The "Street Lights" artist appeared to show genuine remorse, and then Leno made West cry by bringing up his mother, who had died almost two years earlier. "I was fortunate enough to meet your mom, and talk to your mom a number of years ago. What do you think she would've said about this?" Leno asked during the September 2009 interview. West paused and looked overcome with emotion as he seemingly fought back tears before explaining that the VMAs incident helped the rapper realize he was still processing the trauma of his mother's death. "Obviously, I deal with hurt ... and I've never really taken the time off. Just music after music, and tour after tour," he told Leno.

The uncomfortable exchange was shared on YouTube, where many viewers called out Leno for bringing up West's mother. "His mom (with whom he had a 'best friend' relationship) died a year before this...really Jay?" one YouTube viewer wrote. "Jay mentioning his mother seemed a bit unnecessary and out of line," another added.

The late-night host at least seemed engaged with West, which was not the case with the worst guest Leno claims he ever had. Appearing on "The Late Late Show with Craig Ferguson" in December 2014, Leno recalled when "The Bachelorette" star Trista Sutter came on the show in 2003. Leno explained how he had checked out for that interview. "I couldn't be less interested. I've never seen this stupid reality show. I didn't know what it was," he said about Sutter (via ET).