Jack Osbourne | Club Random With Bill Maher
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How do Jack and Bill kick off the conversation and set the tone for the episode?
Hello, Bill Maher.
How are you? I'm good, sir. How are you? Hey, listen. Sorry, I know I just met you. But before I forget, because I get to drinking and I do.
Okay.
Please tell your mother I'm going.
She loves you. That was the first thing she said to me when I told her I was coming in today.
Please, again, before I forget, because I know I will, I tend to do it. But I had such a great time when she was on real time. She did as well. Nothing pleased me more than to kind of fucking, you know, come to her defense. Yes. And, you know, we texted a few times. You know, I always let friendships evolve. Yeah. You know, I don't force them. But just tell her, yes, I could tell I liked her right away. I knew I would, and she's my kind of person.
She was very grateful for... So
we'll all get together sometime before we're dead.
Yeah. LAUGHTER
So how are you? Can I get you a drink?
I'm good. I've got one right here. Cheers.
No, no, alcohol.
No, I do not drink, but I've got a sparkling water. That's so
funny. Like... I always say the kids always do the opposite of their parents, right? Usually, right? I mean... It's a rule of thumb. Don't you think that has something to do with it?
Yeah, but the irony is, though, I have been totally fucking wasted in your presence before, so... You have? Oh, yeah. I
don't remember it, because I must
have been wasted in my presence. Yeah, in my youth, I used to frequent a certain mansion in the... The Playboy Mansion? Yeah. And I
was there serving drinks or something. I don't remember being at the Playboy Mansion. I don't know. So you're talking about the parties. The parties.
Yeah.
I say that because people thought I lived there or something like Jimmy Conn, I think, in the 70s. And of course, I only went to the big parties. Because they were fun. Because they were fun. And it was like four times a year. Yeah. But of course, every time you go, they get a picture of you. Yep. So it does look like you live there. Pretty much. Back when people actually read Playboy magazine.
And saw it. Yeah. And then camera phones ruined everything. Why? I don't know. It just felt like the Playboy Mansion was fun. And then when everyone had iPhones, it no longer became about going to the Playboy Mansion and having fun. It just became about people taking pictures of the Playboy Mansion.
Yeah, I remember in the later days, of course, there's what I call the dead ball era. You know what that is in baseball?
No.
Okay, so you're fucking like half British or some shit.
You don't get
these references, but the dead ball era in baseball was like before Babe Ruth came along.
Okay.
They called it the dead ball era because no one hit home runs. Like Ty Cobb would lead the league with nine, you know. First of all, the ball was different.
Okay.
That's part of it. And they just played a different, scrappier kind of game. And then Babe Ruth changed everything. But for me, the dead ball era was like when he got married. By the way, did you see the sign? I did, yeah. Playmates at play. That was the one that was on the driveway.
When you made the cut. Do you believe
I wound up with that? How did you get that? Auction. Shut up. And it wasn't that much money. Wow. Under 10 grand for that iconic sign. Yeah. I bet you it's worth a lot more already. Yeah. I think that they, but when he died, they auctioned off like the catalog and I'm not an auction person, but somehow they, I guess they figured because.
Because you lived there.
Exactly. Because I lived there, that I would want to see this shit. And it was, I mean, it was like everything the guy ever wore. I mean, his fucking jocks drop, his socks. I mean, it's like when they cleaned out the closet, they cleaned out the closet. Wow. And it was, you know, a lifetime. You know, his car, his, you know. Yeah. I'm sure there was the, you know, the silicone they had lying around
that they used
in the lab and the stuff they used to bolt the tits onto the real housewives. Yeah. You know, but when he got, Matt, when was he? He was like 60-something. Yeah. And then, so that sign came down, and it was children at play because the kids were young.
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Chapters
8 chapters
1
How do Jack and Bill kick off the conversation and set the tone for the episode?
0:01–8:34
2
What does Jack say about his experience with marriage, throuples, and the Congresswoman?
8:34–17:46
3
What dating‑app strategy does Jack recommend for finding a partner?
17:46–28:57
4
How did Jack get involved in rescuing orphans in Ukraine and what challenges did he face?
28:57–41:24
5
What is Jack’s theory on ghosts and why does he think they might exist?
41:24–51:59
6
Why does Bill say he can’t sleep in Europe and what does he attribute it to?
51:59–59:22
7
How do Jack and Bill compare the work of being a comedian versus a TV host?
59:22–1:01:43
8
What final thoughts do Jack and Bill share about relationships, work, and staying curious?
1:01:43–1:02:25