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Hollywood Squares - Season 2 - Episode 07: The Legacy Show
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00:00Drew, how do you think all of us would do
00:03in the Big Brother house?
00:05I feel like I would do really well there.
00:08OK.
00:09Julie, why would I fail?
00:11Drew, you're too nice.
00:13Maybe she can be in the Little Brother house.
00:15Yes.
00:17From Television City in Hollywood, it's Hollywood Squares.
00:23Starring Thomas Lennon, Kristen Schaal, Tim Meadows,
00:27Jason Ritter, Lil Rel Howie, Julie Chan Moonves,
00:34Tashina Arno, and our center square, Drew Barrymore.
00:39And I'm Anna Gasteyer, and we are your Hollywood Squares.
00:44And now your host, Nate Burleson.
00:48Yeah!
00:51Welcome to Hollywood Squares.
00:54What's up, stars?
00:56Whoo!
01:00Man, you look great, Nate.
01:02Man, you look great, Nate.
01:03Hello to our players.
01:04Looking good.
01:04Oh, hello, it's good to have you here.
01:07And a big hello to our center square, Drew Barrymore.
01:10How are you doing?
01:11Hello!
01:13My dearest partner in all things game show, trivia, comedy,
01:17crime.
01:18Thank you, Nate.
01:19It's good to see you.
01:21Hey, Kristen, how are you doing up there?
01:23Oh, hey.
01:25I'm doing great.
01:26I'm on Hollywood Squares!
01:29In Hollywood, considered a star.
01:32I mean, just barely made the cut.
01:34Uh, I've got my cartoon brother, Jason Ritter,
01:38somewhere in there.
01:39Yep.
01:39I'm right here, I'm right here!
01:41How are you doing, man?
01:42I'm loving the mustache.
01:43Oh, thank you very much.
01:44You know, it, like, changes your personality a little bit.
01:47So don't be surprised if I'm a little bit more ruffle-tumble,
01:50a little bit more, uh, a little bit more devil-may-care
01:52than usual.
01:54All right, now that we have met some of our stars,
01:57let's meet our players.
01:58All right, Nikki, go ahead and tell the stars a little bit
02:00about yourself.
02:01Hi, I'm Nikki Jackson.
02:02I'm from Brooklyn, New York.
02:04Okay.
02:05Brooklyn in the house.
02:06Brooklyn, Brooklyn!
02:07Proud mother of two adult children and a 17-year-old dog.
02:11I am a professional organizer extraordinaire.
02:14I go into my client spaces and totally transform
02:17by raising the vibration so that they just feel like
02:19the king and queens of their castle.
02:20Ooh, I like that.
02:21Wow!
02:22Nice pitch!
02:24Vito Angelino, tell the stars a little bit about yourself.
02:27Hello, stars, my name is Vito Angelino.
02:29I'm from Queens, New York.
02:30Okay, Queens.
02:31What?
02:33You got Brooklyn, Queens.
02:35It's a Subway series.
02:37That's who I want.
02:38I am Puerto Rican, Italian, and Hawaiian,
02:40which means I can dance a heck of a hula,
02:42the sexy salsa, and cook some delicious chicken cutlets.
02:46Ooh, all right.
02:48All right, now, here is how we play on Hollywood Squares.
02:52It is your basic game of tic-tac-toe.
02:54You win by getting three squares in a row,
02:55and you can also win by being the first to get five squares.
02:59I will ask the stars a question, and all you have to do
03:02is agree or disagree.
03:03If you get it right, you get the square.
03:05Now, if you get it wrong, that square will go to your opponent.
03:08And at the end of the game, the player with the most money
03:10goes on to our bonus round, where you will have a chance
03:13at $25,000.
03:16Wow.
03:17Hey-oh.
03:18But wait.
03:20There's more.
03:20What else we got, Drew?
03:21I'm glad you mentioned it, Nate.
03:23So there's a secret square.
03:24If you pick it and you get the answer right,
03:27someone gets a fabulous trip of a lifetime.
03:31All right, now, before we get started,
03:33let's show the audience at home who that secret square is.
03:36All right, let's play some Hollywood Squares.
03:41This first round is worth $1,000.
03:45Nikki, you won the coin toss.
03:46Go ahead and pick your star.
03:48I'm going to go with the fabulous Miss Tashina Arnold.
03:51The fabulous.
03:52That's right, Nikki.
03:52My girl.
03:55All right, here we go.
03:56Let's kick this thing off.
03:58Yes, sir.
03:58The Sticky is a TV series inspired
04:00by an actual 2012 heist of what substance?
04:04Let's just hope that it wasn't a sperm bank.
04:07Ooh.
04:10I want to say Elmer's glue.
04:13All right, Nikki, do you agree or disagree?
04:15As I'm thinking the substance, the sticky, icky, icky, oo-wee,
04:20I am going to agree with my girl Tashina Arnold.
04:25Come on.
04:25I hope I got it.
04:25And that is incorrect.
04:28It's actually maple syrup.
04:30I'm sorry, Nikki.
04:32That means X gets the steal.
04:34Vito Angelino, it's on you.
04:36Go ahead and pick your star.
04:37The star of Babes in Toyland, Drew Barrymore.
04:40Oh, my God!
04:41Here we go.
04:44One of my favorite films.
04:46All right, Drew, here we go.
04:48The Washington Monument was the tallest human-made structure
04:51in the world until 1889 when what structure was built?
04:56Well, it turns out Lincoln's was bigger than Washington's.
04:59Oh.
05:01Not just the teeth had wood.
05:03Oh.
05:05You know, I have to admit I'm not perfectly certain on this one.
05:09The Eiffel Tower.
05:11All right.
05:12This is a tough one, but I'm going to go ahead and agree.
05:16You are going to be right because it is the Eiffel Tower.
05:20X gets the square.
05:22Nikki, it's on you.
05:23Go ahead and pick your star.
05:24For the block.
05:26For the block.
05:27I have to go with my guy, Thomas Lennon.
05:29Thomas Lennon.
05:29That makes sense.
05:31Okay, here we go.
05:33Known as liquid gold, colostrum is a substance that comes from what human body part?
05:38Uh, this is unfair because I speak Latin.
05:42Um, colos is the Latin word for colon.
05:46Stram is obviously to strum it.
05:50Um, colostrum comes from, uh, breasts.
05:55All right.
05:56Nikki.
05:57Well, being the mother of two children and, you know, I've got a few of those.
06:01Um.
06:02A few?
06:02Nikki, I'd say just the right amount.
06:06Thank you very much.
06:07I'm going to completely agree with Thomas.
06:10And you would be completely right.
06:13Yes.
06:13It is breasts.
06:14Circle gets the square.
06:16Well done on the block.
06:17Vito Angelino, it's on you.
06:18This game is heating up, baby.
06:20Yeah.
06:20I'm going to go with Tim Meadows.
06:22Tim Meadows.
06:22Oh.
06:23Yes.
06:24Yes.
06:25Here we go, Tim.
06:26What letter is Ana Gasteyer wearing in a 1998 SNL sketch that you two did together
06:32about a kid's TV show that goes awry when its performers wear shirts that spell a curse
06:38word?
06:40Oh, yeah.
06:41I remember this because back then I used to stare at Ana's chest all the time.
06:47Back then?
06:50I do remember that sketch.
06:51It was Jingleheimer Junction.
06:53If I remember right, she was the letter C.
06:57All right.
06:57Do you agree or disagree?
06:58I mean, who am I to disagree?
07:00So I am going to go ahead and agree with Tim Meadows.
07:03And you would be right about that.
07:05Okay.
07:05X gets the square.
07:07All right.
07:08Nikki, it's on you.
07:09I am going to go with my good friend Lil Rel.
07:12Lil Rel.
07:13Lil Rel.
07:13Lil Rel.
07:14Lil Rel.
07:15All right, Lil Rel, here we go.
07:16Lil Rel.
07:17In 2025, when asked who he thought was the most extraordinary scientific mind humanity had
07:23ever produced, Neil deGrasse Tyson said no contest.
07:27Before giving what answer?
07:28For a long time, I thought Doc from Back to the Future was a real scientist.
07:34But if I was to really pick a real scientist, I would think he would say Albert Einstein.
07:39All right.
07:40This is big because you need the block.
07:42I am going to agree with you Lil Rel.
07:47Okay.
07:48It's actually Isaac Newton.
07:50So you would be incorrect.
07:51You cannot win the round on a steal.
07:54So we are going to take a quick break.
07:56And when we come back, let's see if Vito Angelino can take round one for Hollywood Square when we return.
08:11Welcome back to Hollywood Square.
08:12Before we get back into the game, let's check in with a few of our stars.
08:16Now, Drew, we have Julie Chen Mubis in the house.
08:20Yeah, yeah.
08:20So I have a question for you.
08:21Drew, how do you think all of us would do in the Big Brother house?
08:26Well, I feel like I would do really well there.
08:31Okay.
08:32Julie doesn't think so.
08:34Julie, why would I fail?
08:36Not cutthroat enough.
08:38Drew, you're too nice.
08:40Maybe she can be in the little brother house.
08:43Yes.
08:45All right.
08:46We are in the middle of a fierce first round.
08:49And Vito Angelino, it's your turn.
08:50Go ahead and pick your star.
08:52Okay.
08:52His father is one of the best TV dads to have ever been alive.
08:57Jason Ritter.
08:57Jason Ritter.
08:58That's right.
08:59Oh!
09:00Am I in the secret square?
09:01You picked the secret square.
09:03Yes, yes, yes.
09:04Trip, trip, trip, trip, trip, trip, trip, trip, trip, trip, trip, trip, trip, trip, trip.
09:09So if you get this question right, you will win a trip.
09:13Hey, Drew, where could he be going?
09:16Peru.
09:17Peru.
09:18Peru.
09:20Here we go.
09:21What major sporting event is restricted to three-year-olds competing against each other?
09:27Uh, the presidential debates.
09:31I'm just kidding.
09:32We're not going to have any of those anymore.
09:36I think they only use horses only so much before they put them out to pasture.
09:42So I'm going to say, like, the Kentucky Derby.
09:45Okay.
09:46Vito Angelino, this is huge.
09:48Yes.
09:48Because it's for the square, for the round, but then also a trip to Peru.
09:53Do you agree or disagree?
09:55So first off, I am completely unsure.
09:57Me too.
09:58Yeah.
09:59But I'm looking in those beautiful eyes of yours.
10:02Oh.
10:02Okay?
10:04I'm going to agree.
10:05Oh, my God.
10:06That was so romantic.
10:08You got lost in his eyes.
10:11It looks like you're going to be lost in Peru.
10:13Because you are correct!
10:15Woo!
10:15Woo!
10:15It's the Kentucky Derby!
10:17Let's get the square!
10:18And the round!
10:20And the trip!
10:21Congratulations!
10:22Vito Angelino is heading to Peru!
10:25Adventure awaits as you and a guest explore Machu Picchu and Lake Titicaca.
10:31Wander through Peru's colorful open-air markets.
10:35Enjoy amazing food and culture.
10:37And spend a night in the lost city of the Incas.
10:41Collect by travelers for travelers.
10:46All right.
10:47Vito Angelino, you won $1,000 in that first round.
10:51You're also leaving with that trip to Peru.
10:53But it is on to round two.
10:55And now this round is worth $2,500.
10:57Okay.
10:57So if anybody's game, let's get right back into it.
11:01All right, Nikki, it's on you.
11:02Go ahead, pick your star.
11:03We are going to go with Kristen Schaal.
11:06Kristen Schaal!
11:07Thanks, Nikki!
11:09We got this.
11:10All right, Kristen, here we go.
11:12In 1995's Batman Forever, our beloved Drew Barrymore
11:15plays a character with a sweet-sounding name.
11:18What is it?
11:20Diabetes?
11:24I would have to say a face like that and an attitude
11:28that couldn't be on Big Brother.
11:30I think her name was Sugar.
11:32All right.
11:33Nikki, do you agree or disagree?
11:34Okay.
11:35Well, I was thinking candy.
11:37But Kristen, I'm going to agree with you.
11:40Drew, is that correct?
11:43It was Sugar.
11:44It was Sugar!
11:46Circle gets the square!
11:48All right.
11:49Vito Angelino, it's on you.
11:50Okay.
11:51Go ahead and pick your star.
11:52I'm going to go with the beautiful Julie Chan.
11:54Yes!
11:55That's right.
11:57My fellow Queens countrymen.
12:00All right, Julie, here we go.
12:01Along with divorce papers, Shrek ears, and Ozempic,
12:05Uber's 2025 lost and found index reported that
12:08what item was most left behind in its cars?
12:12Well, I know one thing.
12:13It cannot be any worse than what they leave behind
12:16in that Big Brother house.
12:19I know this one because I've done it.
12:22Cell phone.
12:23Okay.
12:24A part of me is not too confident,
12:26but I'm going to go ahead and agree.
12:28Cell phones.
12:29And you would be correct.
12:31It is phones.
12:32Okay.
12:32Wow.
12:33X gets the square.
12:351.7 million people left their phones.
12:38Idiots!
12:39They're all idiots!
12:41Come on.
12:42Guilty.
12:44All right, Nikki, it's on you.
12:46Okay.
12:46We're going to go with Tim Meadows.
12:47Tim Meadows!
12:54All right, Tim.
12:55Here we go.
12:56Whose classic slogan is,
12:58have it your way?
13:00Definitely not the people at the DMV.
13:04Oh, of course, that's Wendy's.
13:07All right.
13:08Nikki, do you agree or disagree?
13:09Really hate to disagree with you.
13:10However, I believe it's Burger King,
13:12and I'm going to have it my way and say Burger King.
13:14I disagree.
13:16I guess you put me in my place.
13:18You know what?
13:20That was a whopper of a lie,
13:21because it is Burger King!
13:23Yeah!
13:23You are correct!
13:24Circle gets the square.
13:26All right.
13:26It's time for a quick break for Hollywood Squares
13:29when we return.
13:30Woo!
13:39Welcome back to Hollywood Squares.
13:41Vito Angelino banked $1,000 in that trip to Peru
13:45in the first round.
13:47But Nikki can take round two,
13:49and you'll be taking home $2,500 if you do.
13:52Right.
13:53But Vito Angelino, it is on you.
13:54It's your turn.
13:55Go ahead and pick your star.
13:57I got to keep it rolling.
13:59Thomas Lennon.
13:59Thomas Lennon for the block.
14:02Come on.
14:02Come on.
14:03All right, here we go, Thomas.
14:04Harrison Ford once told David Blaine to
14:07get the bleep out of my house
14:08after the magician made what item appear
14:11in an uncut orange?
14:13It was Calista Flockhart.
14:18He pulled a playing card.
14:22A playing card, all right.
14:23For David Blaine, the card sounds about right.
14:25I'm going to go ahead and agree.
14:28And you are going to get the block.
14:29X gets the square.
14:30It was a playing card.
14:32All right, Nikki, it's on you.
14:34Pick your star.
14:34We are going to go with Mr. Jason Ritter.
14:38Jason Ritter.
14:42Okay, Jay, here we go.
14:43Eventually, getting a small tweak,
14:45what was the original name of the band Blink 182?
14:49Was Blink 1 through 181 taken already?
14:54Uh, I think I'm going to say Wink 182.
14:59If it was a tiny twink, just one eye.
15:02A twink to a wink.
15:03From a blink to a wink.
15:04That's a twink.
15:05Somebody's got twinks on the mind.
15:07All right.
15:09Okay, he's going with Wink 182.
15:13Not twink 182.
15:14Yeah.
15:15That's a completely different band.
15:16Yes, totally different.
15:17Also wonderful.
15:19I am not familiar with the history of this band,
15:22so I'm going to have to disagree.
15:27And you would be correct.
15:30Circle gets the square.
15:32It's actually just Blink.
15:34I twinked the wrong part.
15:35Yeah, you did.
15:37All right, Vito Angelino, so why don't you pick your star?
15:39For another block,
15:40hopefully I'd be welcome in her neighborhood,
15:42the wonderful Tashina.
15:44Tashina for the block.
15:45Tashina!
15:46Come on, baby.
15:47Come on over to my neighborhood.
15:49All right, here we go.
15:51Rob Lowe once told a Hollywood tour guide
15:53to get better at your job after the guide mistook him for who?
15:58Samuel L. Jackson.
16:02I'm going to say they look alike.
16:05John Stamos.
16:06Okay, Tashina is saying...
16:08You know all white people look alike, so...
16:11Yeah.
16:13Vito Angelino.
16:14So I've actually seen that clip.
16:16Oh.
16:17Oh.
16:17Oh.
16:18I do agree.
16:20Come on, Queens.
16:21Come on, Queens.
16:22X gets the square in the block.
16:27Way to go.
16:28Woo!
16:29Oh.
16:30So that sound means that time is up.
16:34So here's what we're going to do in this round.
16:36We are going to give you $500 for each square that you have,
16:38which means, Nikki, you have a total of $1,500.
16:42Okay.
16:42Not bad.
16:43Okay.
16:43So congratulations.
16:44You are not leaving empty-handed.
16:46And Vito Angelino, you have a total of $2,500
16:50and that trip to Peru.
16:52Yep.
16:52Which means you are going to the bonus round.
16:55And when we come back, Vito Angelino is going to be playing
16:58for $25,000.
17:07Welcome back to Hollywood Squares.
17:11Woo!
17:11Drew.
17:12Wait.
17:13Where's Drew?
17:15What are you doing?
17:17Still trying to get a job.
17:20You auditioning?
17:21I'm sorry.
17:22Who are you?
17:23Uh-huh.
17:24Behind me, I thought you were going to stab me in the back.
17:27So maybe you do have what it takes to be in the Big Brother house.
17:31She said, I have a chance.
17:35Expect the unexpected.
17:40She's lying to you, Drew.
17:43I'm going to get on damn Big Brother.
17:46All right, now, Vito Angelino has racked up a cool $2,500
17:50and a trip to Peru.
17:55Now, it is time to play the bonus round.
17:57Where you will have a chance at winning $25,000.
18:04So, Vito Angelino, any idea of what you would do with all that money?
18:08Definitely.
18:09This money would mean a lot to my family and I.
18:11During the Palisades Fire, my wife lost her small business.
18:14Aw.
18:14So, this would go help towards rebuilding that.
18:17Well, we all want that to happen.
18:21All right, now, here's how the bonus round works.
18:23You are going to have 60 seconds.
18:24I will read a statement about each star.
18:26All you have to do is agree or disagree.
18:28For everyone that you get correct, you will earn that square.
18:31Now, here's the thing.
18:32Every star up there has an envelope, but only one of them
18:35holds a card worth $25,000.
18:38The Monvino Angelino.
18:40Okay, let's put 60 seconds on the clock.
18:46Here we go.
18:48Thomas Lennon's childhood pet was a box turtle named Alan.
18:53Agree.
18:54Incorrect.
18:55Kristin Shaw's nickname for her husband is Cheddar Bay Biscuit.
19:00Disagree.
19:01Correct.
19:02Tim Meadows voiced a character named Chet Handsome Man.
19:07Disagree.
19:08Incorrect.
19:10Anna Gasteyer once said that she can drive a stick shift
19:13and quietly judges men who don't know how.
19:15Agree.
19:16Correct.
19:17Drew Barrymore hates garlic.
19:19Disagree.
19:20Incorrect.
19:21Jason Ritter is an avid knitter.
19:24Ooh.
19:25Agree.
19:27Incorrect.
19:28Lil Rail once said in an interview that he thinks about
19:30being a Jedi way too much.
19:32Ooh.
19:34Agree.
19:34Correct.
19:35Julietin Moonves is a competitive archer at the level of Bowman first class.
19:40Ooh.
19:41Disagree.
19:42Correct.
19:42Tashina Arnold performs around L.A. with her band No Pressure.
19:48Disagree.
19:49Incorrect.
19:51You got four out of the nine.
19:53That's solid.
19:53All you need is one.
19:55All you need is one.
19:56All you need is one.
19:58Stars.
19:58Show us the money.
20:03Kristen.
20:07Lil Rail.
20:10Ah.
20:13Julie.
20:14Ah.
20:16Ana.
20:24Had the $25,000.
20:27So that's adding to his earlier winnings.
20:30He has now won a grand total of $27,500 bucks in the trip to Peru.
20:37Thank you to all of our stars and our center square to Barrymore.
20:42I'm your host Nate Burleson.
20:43Join us next time on Hollywood Square.
20:47Whoo!
20:48Whoo!
21:16Oh, good day.
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