It takes two to tango, and in this case, it took two celebrities to make television viewers deeply uncomfortable. When Madonna stopped by the David Letterman show in 1994, things quickly got weird. First, David began pressuring her to kiss a random person in the audience, refusing to take no for an answer.
Then, Madonna made everyone cringe when she revealed she had given David a pair of her undergarments, telling him to show the audience. The interview was so uncomfortable and inappropriate we couldn’t turn it off fast enough!
Jesse Eisenberg’s Strange Attempt at Flirting Goes Viral
While promoting his magician-themed film “Now You See Me”, actor Jesse Eisenberg subjected us to an interview that we really wish we hadn’t seen. The actor, who was being interviewed by entertainment reporter Romina Puga, began flirting with the presenter in the most awkward way we’ve ever seen.
From snippy banter to Romina jokingly (we hope) referring to her guest as a “jerk” to her referencing them being in a relationship — the whole thing made us feel confused. He may have magic skills, but his flirting skills need some brushing up!
Mila Kunis Shuts Down Reporter in Two Languages!
It doesn’t hurt to have someone on your team who speaks the local language. Just ask Justin Timberlake! When he and “Friends With Benefits” co-star Mila Kunis were being interviewed by the Russian press, Mila (who speaks Russian fluently) immediately intervened after Justin was asked a rude question.
After the reporter asked why Justin was now appearing in movies (implying he should stick to music), a visibly irked Mila shot back asking the reporter, “what kind of question is that? Why are YOU here?” The video must be seen to be believed!
Ellen’s Outrageous Way to Get Mariah Carey to Confess
While it’s quite common for talk show hosts to tease answers out of their celebrity guests, it’s often done in a tasteful and humorous way. Sadly, that wasn’t the case when singer Mariah Carey visited the Ellen DeGeneres show in 2008.
The host demanded that Mariah address the rumors of her pregnancy, even pressuring her to drink an alcoholic beverage to prove that she wasn’t pregnant! Naturally, the mom-to-be was forced to admit her very private news, later calling the event “extremely uncomfortable”. Not cool, Ellen!
Madonna + Courtney Love = Epic Levels of Awkwardness
When two major music icons collide, there’s bound to be an uncomfortable level of tension. In 1995, while being interviewed at the MTV Video Music Awards, Madonna’s interview was interrupted by Courtney throwing a makeup compact at her. “Courtney Love is in dire need of attention right now,” Madonna remarked
After being invited to join the interview, a clearly inebriated Courtney and Madonna engaged in a conversation that ran the gamut from uncomfortable to plain catty. Madonna even implied that Courtney should leave show business. A must-see in award interview history!