Macaulay Culkin and Brenda Song have been together since 2017, but does all that time together mean they know each other’s careers inside and out? In this playful Cosmo Couples quiz, the two get super competitive, from Brenda nailing which co-star bit Macaulay’s finger (and kissing his booboo) to Macaulay calling London Tipton’s catchphrase a "layup"—yay him! Watch as they realize they both starred in Christmas movies, share their love for Jamie Lee Curtis, and rave about each other’s work in the sweetest way. Brenda confidently declares, “We both won at life, but I won at these quizzes”—but who will truly come out on top?
I could hear him karaoke-ing from another backyard. I was like, I know that karaoke.
Yep, I'm a crooner. What can I say? I'm a crooner.
Hi, I'm Macaulay Culkin.
And I'm Brenda Song. And today, we are going to see who knows each other's career better.
I think I'm going to do okay. I'm just, I'm very competitive. And I know we're not keeping score, but I'm going to keep mental score.
No, we're going to keep score.
Alright, well, good luck.
Oh yeah, good luck.
Are you ready, honey?
Yes, I'm ready.
Okay, what was my first acting gig?
Santa Claus with Muscles?
Nope.
I never saw Santa Claus with Muscles. Sorry.
How dare you? How dare you? My best work. My best work.
I just knew you were in it.
See? Both of us star in Christmas movies.
Yeah, true. Wow, yeah.
First commercial was Little Caesar's Pizza commercial.
Okay.
And first, like, show was Thunder Alley.
Maybe I'm going to win this.
Alright, well, fine.
Okay, which role did I prepare for by visiting someone in prison?
Party Monster?
Yes.
Like Oleg.
Yes, yes, yes.
Party Monster is one of my favorite movies. I love that movie.
Oh, thanks.
So you're the one.
How dare you?
What was Lennon Tiffin's go-to catchphrase?
Yay me.
More shopping. Yay me.
That's easy. That's easy. That's a layup.
Alright, alright.
That's a layup.
Okay.
Which past co-star left a permanent scar on my finger?
Joe Pesci. In Home Alone, he bit your finger when you were hanging on the back of the wall.
You told me that story.
There it is. There it is.
Can you kiss my booboo?
Thank you, baby.
Do you remember your reaction when he bit your finger?
Yeah, I said, ow.
I was like, ah.
During rehearsal, and we were kind of just rehearsing, and nobody was paying attention,
and I could see his face, and he was like, oh my god, I bit a child.
And it was a little bit of like, don't tell anyone, kid.
I didn't snitch. I didn't snitch on him.
It was until I was an adult where I actually told that story.
I'm not even sure if I know this one.
What was my first titular role? Tell me.
Oh, gosh.
I think it's the Netflix one that you did.
Something Strange or Something. No?
I think it's Wendy Wu.
Oh, yeah. Homecoming Warrior.
Yep.
Yes.
Am I wrong?
Oh, I got my own quiz right.
Yes, yes, yes.
Oh, man.
We had the poster up in the house for a while.
It's just an amazing poster.
Like, I wish I mocked that up.
Hey, I actually had to do that.
They had me on, like, I was in a harness.
They had to pull me up, and I had to kick and smile at the same time, honey.
Oh, wow.
Multi-talented over here.
I know, look at you.
He's so lucky.
Yeah, he won't miss kick-smile over here.
Luckily, I never had to use my skills on you, honey.
Maybe strict your stuff after this.
Oh, god. Okay, continue. Next question.
All right.
All right, this one's not too hard.
Okay.
In which 2004 comedy did I play Mandy Moore's brother?
Saved.
Yeah.
Yeah, I have.
I still haven't seen it, though.
You're not the only one.
Which of your former co-stars did I star alongside in The Last Showgirl?
Oh, Jamie Lee Curtis.
The best.
She's the best.
She was the sweetest.
I forced Mac to come up to the shoot with me, and we lived in Vegas for a month.
Yep.
And we walked in, and Jamie writes children's books.
And she had a stack of children's books that she personalized to our kids.
Yeah, each one of them.
Each one to our kids.
It was the sweetest thing.
I'd never met her, and she's just wonderful.
Yeah, and visited on set.
Yeah.
And just hadn't seen her in, like, 30 years.
She's the best.
Yeah.
She's the best.
I miss her.
What was the last film I appeared in before going on a decades-long hiatus?
I don't know if it's Rich Rich or Getting Even with Dad.
And then you went on a big break.
Oh, gosh.
Hold on.
I'll say Getting Even with Dad.
Rich Rich?
Dang it!
I was kind of right.
I knew it was one of those two.
Yeah, yeah.
No, you certainly did.
And then you did a big break, and then it's Saved in the Party Monster.
Yeah.
You had the coin flip, and you blew it.
I feel like I get, like, half a point.
Nah.
How dare you?
I don't know if you'll know this.
Maybe you will.
All right.
What TV series did I guest star on alongside America Ferrera?
Oh, my goodness.
I kind of know this one.
Hold on.
New Girl?
No.
Superstore.
You were in Superstore?
Yeah, Superstore.
Yep.
I had absolutely no idea that you were on that show.
I did.
Yeah.
Okay.
This one shouldn't be too hard.
Okay.
Name three actresses who have played my mom on screen.
Oh, I think you showed me this.
Hold on.
One of them is Farrah Fawcett.
Yeah.
Nice.
Yes.
Catherine O'Hara.
Yeah, that's way up.
And then Walter.
Ooh.
That's a deep cut.
I know.
That's who I'm trying to think of, but I can't.
That's a deep pull.
I mean, I pulled out Farrah Fawcett, okay?
Yeah, that's a good pull.
Okay.
That's a strong pull.
I don't know the third one.
The one you were trying to pull was Patricia Clarkson.
That's what it was.
Oh!
Yeah.
Patricia Clarkson.
She played my mom in my first movie.
Yes.
In Rocket Gibraltar.
Yes, yes.
So I get like three quarters of a point.
No.
Incomplete.
Okay.
In which Fox sitcom did my on-screen love interest steal my cat?
Oh, I'm going to go back to New Girl.
Yeah, you got it.
Yes, yes, yes.
Lamorne.
Who you just met, actually.
Oh, indeed.
Yes.
Finish this iconic My Girl line.
Okay.
You can't marry a teacher.
It's blank.
Oh, no.
I don't know it.
It's a crime.
No.
It's against the law.
Yeah.
I'm mad at myself.
What's your favorite line from any of your films?
Sometimes, like, you know, like, I pay something for cash, and then, like, you know, they only
give me, like, a buck or something.
Just keep the change.
Keep the change, you filthy animal.
They just go, oh, no, never mind.
Your money's no good here.
Look at me.
Name three animated series that I have starred in.
Amphibia.
Mm-hmm.
Proud Family.
No, Phineas and Ferb.
Both.
No.
Oh, and I don't know.
I don't.
Okay, well, I was in The Proud Family.
Okay, I knew that one.
And Blue-Eyed Samurai.
Oh, yeah, duh.
How gross was it?
I didn't know you were going to be so mad about that.
We just went to the after party.
I know.
We just started season two.
The low-hanging fruit, and I couldn't pluck it.
I don't think you're going to get this one, but maybe.
How dare you?
I don't know.
What's my character's name in Righteous Gemstones?
Dang it.
I don't think you're going to get this one.
No, I don't.
Baby Billy Jr.
No, no.
I'm Harmon.
Harmon.
Yeah.
It's not like a Dave.
Okay, all right.
Yeah.
I don't think you're going to get this one either.
Okay.
Finish this iconic doll face line.
Okay, goodness.
You need to find an apartment that's aspirational.
Something that says, blank.
Oh, my goodness.
I'm going to guess.
How dare you?
I put the sexy in successful.
Oh, okay.
Yes.
You don't remember.
You're blanking your line.
You don't know.
I don't know.
I never said.
I was going, uh, no.
You were in doll face, too.
I know, yeah.
That was not my episode.
It's not.
I clearly haven't seen it.
What song did Timmy Gleason lip sync in Getting Even with Dad?
Oh, no.
Honey, I'll be honest.
I never saw that.
I never saw it, either.
Really?
No, I saw it.
I went to the premiere.
I don't know.
But I remember your, like, mullet-y haircut, though.
Yes, exactly, yeah.
What was it?
Me, too.
I'm sure it's, uh, Do You Love Me?
Maybe we'll watch that.
I'm forcing you to watch all your old movies.
We can skip that one.
Let's go.
Do you guys have a go-to karaoke song?
Oh, I.
Mine.
Oh, yes.
My Way.
Yeah.
Frank Sinatra.
Our neighbors were having a party where they were karaoke-ing.
And she, like, she didn't want to go or she was sick or something.
I was putting the kids to bed.
Yeah, yeah.
She heard My Way being sung.
I texted her.
I was like, are you karaoke-ing right now?
Are you singing My Way?
Like, yes, here.
I could hear him karaoke-ing from another backyard.
I was like, I know that karaoke.
Yep.
I'm a crooner.
What can I say?
I'm a crooner.
All right.
It's time for the quickie.
We have 30 seconds to answer as many of these questions as we can.
Who's better at auditioning?
Yeah.
Who can memorize lines fastest?
Who's more likely to steal something from set?
Oh, I am.
Yes, you.
Who would make the better director?
You.
I'm a better producer.
You're probably a better director.
Who's more likely to show up to set on time?
Me.
Oh, yeah.
Probably you, though.
Who is better at early call times?
Me.
Yeah.
If we weren't actors, who would make the better PA?
Me.
Yeah.
Who's most likely to leave the wrap party last?
You.
Yeah.
We're quick.
Well, yeah, we get it.
We're the best.
We both won at life, but I won at these quizzes.
I don't know about that.
But all right, fine.
Thanks so much for watching.
Be sure to check out our Cosmo cover.