In January 2007, Adam Carolla broadcast his radio show, “The Adam Carolla Show,” live from the Playboy Mansion in Los Angeles. Among the various guests that day was none other than our country’s most aggressively online son, Donald Trump Jr., who took the opportunity to talk about his dick, his father’s dick, how the two compare, and just how much of a hardship it is to be surrounded by Playboy Playmates when you have a pregnant wife in tow.
The since-forgotten segment, which appears to have been taken offline but was preserved by the Internet Archive, lasts a little over 13 minutes and covers a number of topics.
On his predicament
Trump Jr.: Can you believe the hell I’m going through? I’m at the Playboy Mansion with a pregnant wife! It doesn’t get worse than that, does it? Now, I love my wife, but that is rough. And I’m going to pay for these statements later on tonight. I’m gonna pay.
On Melania’s age
Host: Donald, your pregnant wife is chatting up Melania, your stepmother. What is the age gap between those two?
Trump Jr.: Much closer than most would ever guesstimate. Probably about five years, six years.
Host: Which one’s older?
Trump Jr.: My wife.
Trump Jr.: No, I’m just kidding.
On coal miners
Host: Question one: Did you always plan to follow in your father’s footsteps, meaning become a billionaire and bone hot chicks?
Trump Jr.: I think the answer to that is an obvious yes. [Sarcastically] No, I wanted to go to work in a coal mine.
On Miss USA
Host: Number two: Did you ever have sex with Miss USA?
Trump Jr.: Which one?
Trump Jr.: I’m just kidding, baby!
On Melania’s hotness:
Host: Are you attracted to your stepmother?
Trump Jr.: I think she’s a very lovely lady.
On his inheritance:
Host: And the last one is: Have you ever thought about killing your dad for his money?
Trump Jr.: Well, you know…
Host: That’s a yes.
On whether he or his dad has the larger penis:
Host: I got one question, Donald Jr.: When you and your pops are in the shower, who’s got the bigger package? You know what I’m saying.
Trump Jr.: You know, and I will get fired for this, but I’m never going to say that I don’t. I will get fired for that. By the way, they’re both pretty substantial I think.
You can listen to the 2007 Carolla segment in full here.
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