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As you may have heard, yesterday Larry King announced that he was going to “hang up his nightly suspenders” and end Larry King Live after 25 years on the air. Why should you care? Good question.

Turns out, over the past two decades King has interviewed countless musicians—and a lot of those interviews have been awesomely awkward. In honor of King’s retirement, we decided to relive some of the most awkward musical interviews he has ever conducted. Say what you will about King, but we have no idea who has the personality to carry on this aspect of his legacy.

Chris Brown, 2009

First of all, being asked why you beat your girlfriend is going to be uncomfortable no matter who is asking the question. However, doing it on live television with your mom sitting next to you has got to be the most awkward situation ever.

Thankfully, using his journalistic wisdom, King decided to open with a curveball by telling Brown, “This had to be the worst period of your life.” When Brown replied “possibly,” King incredulously repeated back to him, “Possibly?” (Yeah, we get it, the dude’s life sucks, Larry.)

But if that weren’t enough, he informed Brown that “what happened happened, so you have to accept the consequences” even though Brown had just got back from the sentencing with an actual judge.

Madonna, 1999

As usual, King started his interview with Madonna by asking her something really deep—like, how she got her name. Then he went on to tell her that the phrase “performance artist” also includes acting and thus suggested that she call herself that moving forward. (This was clearly sound advice.)

The best part, however, was when King acted super surprised when Madonna said the best part of being famous was getting free clothes. Umm, she is Madonna, of course she gets free clothes.

T.I., 2010

If you had to imagine the polar opposite of Larry King, you’d probably come up with someone pretty similar to T.I. His interview with the rapper started awkwardly with T.I. walking across the soundstage to sit down as King read his rap sheet. Then King went through all of the guns that T.I. bought and asked multiple times who he thought “was after him.” Let’s be real, if T.I. knew who was after him he probably wouldn’t have needed an arsenal of firepower at his disposal.

That said, we respect the way that T.I. politely answered King’s questions without getting frustrated or annoyed. Sadly, we can’t say the same thing about former beauty pageant contests.

Lady Gaga, 2010

In this recent gem, it was awesome to hear King say the phrase “self-proclaimed freak” when introducing a pop star he had probably never actually listened to. It was also awesome that the “Telephone” star showed up on the program wearing sunglasses, a tie and fuzzy suspenders, clearly imitating King’s style.

However, our favorite moment was when King asked Gaga when she knew that she wanted to be a performer and she responded, “When I was in my mother’s womb.” King obviously had no idea if she was kidding or not so he kind of half laughed, let there be a few seconds of uncomfortable silence and then followed it up with more scripted questions.

Tom DeLonge, 2006

We have no idea who told Tom DeLonge that it would be a good idea to go on Larry King Live to promote Angels & Airwaves‘ We Don’t Need To Whisper. But we’re really glad that they did. You’ve got to give King credit for spending the first three minutes of this interview asking blunt questions like “Did you get married young?” and “You’re interested in things other than music, right?” proving that if anything, King is tactful.