-Chelsea, in your documentary,
you revisit a lot of moments in you life.
And so I thought before you go,
we could play a game called "First, Last, Best, Worst."
[ Fingers click ]
[ Cheers and applause ]
♪♪
-Wasn't that so fancy? So fancy!
Here's how it works.
I'll give you a topic, like "Person You Kissed,"
and then you'll pick a paddle and share either
your first, last, best, or worst experience.
But here's the thing --
you can only use a paddle once, so choose wisely.
-Oh. -Got it? Are you ready?
-I have to sit up straight for this.
-Yeah, all right, here we go. -Hold on a second.
Okay, hold on. Let me uncross my legs.
-It's a whole thing. -Yeah, yeah, yeah.
Okay, first prompt -- Celebrity encounter.
First, last, best, or worst. Your choice.
-Um... -You pick it up.
-Okay. -First celebrity encounter.
What's the story?
-First celebrity encounter, I think, was meeting Jane Fonda.
-Mm-hmm. -And I couldn't talk.
And I -- -You're a big fan?
-Well, yeah, I was just so intimidated by her,
and I just went -- and luckily she's like,
"I know who you are."
And I said, "Oh, I'm Chelsea Handler."
She said, "I just said I know who you are."
[ Laughter ]
And then I turned around, and I said, "Okay, bye."
[ Laughter ] She said, "No, come back."
That was the first time I met a major celebrity.
-Did you overthink it to death afterwards?
'Cause that's what I do. After I met you, I was like,
"What did you say to Chelsea Handler?!"
-Oh, yeah, I'm like, "I hope she doesn't remember me."
Like, "I want to be friends with her eventually."
And, eventually, I mean, I did become friends with her,
and she doesn't even remember it.
So, yes, I overthought it, and I mean, that happens, like,
the first 10 celebrities you meet.
And then, eventually, they just become
like regular people, too. As you may know.
As you'll find out. [ Laughter ]
-All right, next prompt.
The time -- Ooh, this is a good one.
-So do I put this one down? -You just throw that over there.
-Do I eat it? Okay. -Okay.
You smoke it. Okay. [ Laughter ]
Time you broke the law.
You got three paddles to choose from --
Last, best, and worst.
-Uh, uh... Okay, I'll just do the last.
-Okay. -'Cause it's closest.
The last time I broke the law --
-Because you could do one for either.
-Technic-- [ Laughter ]
Technically, the last time I broke the law
was the last time I was at an airport
when I took a book, and I didn't have the patience
to wait for that transaction at the Hudson Booksellers store.
The slowness of the transaction.
So I just took money out of my wallet,
and I waved it at the security camera.
I'm like, "It's me. Don't want to wait in this line.
Here." [ Laughter ]
Put it on the shelf, and I walked out with the book.
-How much money did you leave? -I left 40 bucks.
I think the book was $20, so they got a tip.
-Amazing! What book was it?
-I don't remember.
-"How to be a Bawse," by Lilly Singh?
That's so sweet. [ Laughter ]
That's so sweet. [ Cheers and applause ]
Oh, my gosh! Wow, that's so -- wow, okay.
You can throw that away. -All right.
Hold on. Let me move these closer.
-All right. So, you have two paddles left,
best and worst. -Okay.
Okay. -I can't wait for this.
-Okay. This is going to get ugly.
-The prompt is "High experience."
-High experience. Uh, okay.
-Best or worst. -I'll say --
Well, okay, I'll say the worst high experience was --
This was before cannabis was legal.
-So this also could've been the time you broke the law.
[ Laughter ] Could have been either.
-Right, yes, yes, yes. You're following very closely.
[ Laughter ]
I took an edible, a cookie,
that was made from your home country, Canada.
-I was like, "India?" [ Laughter ]
-From your hinterland.
-Just a masala cookie with weed in it.
[ Laughter ]
-And I ate a cookie, and I was watching a movie,
and when that movie ended, I got up to leave
the movie theater only to find out that I was on an airplane.
[ Laughter ]
-What -- -So that wasn't the worst,
but it was the most surprising. -So, wait, wait.
Did you physically get up and try to leave?
-Oh, yeah, got my bag out of the overhead bin.
Got up, was like, "Oh, wait. Let me get my stuff."
Because that's how you leave a movie theater.
You get your luggage and then you wheel it up to the front,
and then the window, I was like, "Oh, whoopsie doodle."
I was like, "You're on a plane, girl.
You need to get your act together."
-Relatable. [ Laughter ]
You got one paddle left, and it's for best.
-Well, I guess this better be my best.
-Just best. Oh, and it's good one.
Okay. Your best one-night stand.
-I'm gonna take some liberty on this story,
because I've heard -- I have a friend
that has a better one-night-stand story than I do.
So -- And this is the -- This wasn't her best,
but it was the best for me to hear.
She hooked up with a --
Well, no, she didn't even hook with a guy.
She slept over at somebody's house.
Yeah, the guy did hook up. Okay, they hooked up.
-What's the definition of that, by the way?
-I don't know. Maybe fooling around or sex.
I'm not sure. It doesn't -- Yeah.
[ Laughter ] But good question.
-I always wanted to know.
-Yeah, I mean it's a little late for you to find that out.
-Yeah. -Okay.
-Yes, it is.
It's a little late with Lilly Singh.
-And she hooked up with a guy and then went to go
to the bathroom in the middle of the night
and ran into his hamper.
And when she woke up, he legs were like this,
and her friend said, "Hey, sweetie pie,
you're in a hamper." [ Laughter ]
And she had thought the hamper was the toilet.
[ Audience groans ] -No.
-You guys don't think that's a fun story?
[ Laughter ] -Oh!
-You sound sad for her. [ Laughter ]
-So, you've obviously had so many
amazing experiences in your life.
What is an experience you haven't had yet?
Like, what do you -- what else do you want to do?
What else is out there for Chelsea Handler?
-Oh, well, what do I want to do?
I mean, I don't know.
I'm gonna just -- What do I want to do?
I guess I should probably start a family.
-Do you mean a family that's different from this family?
'Cause you recently posted this picture
of you and Martha Stewart side-by-side.
-Oh. -With your identical dogs.
Is this the type of family you want?
Or are you thinking something beyond this?
-Yeah, that's pretty much the kind of family
I'm capable of having. I mean, you know,
I wouldn't ever go through with a pregnancy,
so that's out for me. [ Laughter ]
And Martha Stewart has always been one of my idols.
Not really, but I do love her.
-Do you feel like -- 'cause you guys --
Do you have things in similar? -Yeah, yeah.
She says she doesn't smoke weed, but I think she does.
[ Laughter ] And I started cooking recently.
I started cooking for -- almost professionally.
-Yeah. [ Laughter ]
-On Instagram. I make videos about my recipes,
and people are really responding to them.
So we have that in common. We both wear denim.
And, uh... [ Laughter ]
She's been to prison, and I've actually also been to prison.
-Okay. Wow, okay.
-Mine was just for one night. I got arrested and that was it.
But hers was for a long time,
so I hope that doesn't happen to me.
You know? -Yeah, okay.
Did you get arrested for trying to exit an airplane?
-Possibly. I mean, I've been arrested and it's on the record.
[ Voice breaking ] You can google it.
[ Laughter ]
That is all the time we've got.
My thanks to the wonderful Chelsea Handler
for being on the show. [ Cheers and applause ]
You can find tickets to her stand-up tour on livenation.com.