Which Try Guy Is The Best Boss?

– Welcome to the 2nd Try Casino! Today, it's another rousing edition of “Which Boss Knows Best?” (all cheering) – As soon as you said that, my chest started getting hot! (all cheering) – [Miles] Each boss will be guessing which piece of fun trivia belongs to one of our 11 employees.

(all cheering) – I don't like this at all! (upbeat music) – [Miles] Let's meet the bosses.

– What's up, I'm Zach, I'm the Start-Up Boss.

I'm a chilled boss, you know.

I'm just here to keepthings casual and fun.

– What's up? I'm Ned, I'm the tech CEO.

I want everyone here to think different.

By 2030, the “Try Guys”could put a man on the moon of Jupiter! – Well, howdy there.

I am Cowboy Boss.

They say the internet is the Wild West, and it sure is.

– Hello, I'm Eugene, and I'm the Cool Boss.

– Eugene, how do you thinkyou're gonna do today? – I'm going to, for sure.

(upbeat music) – Each one of our fourbosses will be reaching into the bowl of trivia tofind one fact about one of us.

They'll then be nominatingone of the 11 of us to see who they think it is.

– Today, we are gonna be guessingabout our production team.

We have our producers, Nick and Rachel.

Our production manager, Alexandria.

We have our editingteam, Elliot, Devlin, YB.

And our assistant editor, Will.

We have our social media manager, Kaylin.

We have our shootingteam, Miles and Jonathan.

And of course, we have the wonderful Sam.

Our game is broken down intothree types of questions.

Green for one point, yellow for two points, and red for, you guessed it, three points.

– Are these facts thatwe would have learned like in water cooler conversation? – These are facts thatany good boss should know.

– I think some of you I know okay, others maybe I don't know as well.

In general, I think thisis just a recipe for us to get brutally embarrassed.

– I think I know the staff well.

You know, we kick it.

I think I'm gonna do pretty okay.

– I think I'm gonna lose.

Yeah, I'm pretty sureI'm at gunning for third, but I think I'm gonna lose.

(upbeat music) – Are you gonna keep theaccent up the whole game? – Well, I am a cowboy.

(all laughing) I can drive a forklift.

(tense dramatic music) – [Zach] I know the answer to this.

– Oh, wow.

– Whoa.

– I'm going to go last.

– Then I'll guess before you.

– I'm locking my answer in.

– I believe it is Nick.

– I also am guessing Nick.

– Will's my guy.

– Well, I'm gonna tell you that, Eugene, I think you're right.

I am the boss of the people.

I talk to y'all.

I hang out, and I know thatWill has this crazy past where he worked in this wacky factory, and had ridiculous co-workers, and he's got some stories.

Will, put that hand upand tell me I'm right.

– Now, Nick, concerningthe forklift, is it you? – Miles, it's not.

– Ooh.

It'd be funnier if you went, “Miles.

” (all laughing) – Will, is it you? – No? – I'd like to just say, thank you for thinking that I could, Zach.

(tense dramatic music) – [Ned] Wow, Zach.

– No! – The boss of the people!- Wow.

– Whoa, the first question! – If the person who isqualified to drive a forklift could please raise their hand.

It's Jonathan!- Oh man.

– [Jonathan] I worked at a brewery.

There were guys at thebrewery who would do burnouts, I was not one of them.

– I managed a hot dogstand as my summer job between high school and college.

(tense dramatic music) – I'm gonna give this one to Sam.

I like the idea of him walking out, walking out to the employees and yelling, “We need more wieners!” Could you yell that real quick? – We need more wieners! – I'm giving it to Alexandria.

– I think someone who could handle it would be Mr.


– I've got to look at the word, manage, and potentially pick oneof our management material.

Yeah, I guess I'll pickRachel, our producer, who manages our team.

Maybe she also managed a hot dog stand.

– Alexandria, was it you?- Damn it.

– Sam, was it you? – [Eugene] Aw, damn it! – [Miles] Elliot, was it you? – [Keith] Shit.

– Oh, come on, big money, big money, big money! – [Miles] Rachel, did youmanage a hot dog stand? (all groaning) – Tricky, tricky.

– Would the manager of a hot dog stand please raise your hand.

– Get your hot dogs here!(all cheering) And they were Chicago-style, baby.

Cucumbers, tomatoes, pickles, celery, salt, no ketchup, only mustard.

– The fact is I played the saxophone.

(tense dramatic music) – [Keith] Could everybody do this? (all laughing) – I'm gonna say Devlin again.

– Right now, my mind's flippingbetween Kaylin and Elliot.

I'm not sure why, that's just my gut.

I'm gonna go with Elliot.

– (beep) it, I'm guessing Miles.

– You all mean a lot to me, but there's only one sax man in my heart, and I, too, am going with Elliot.

– Miles, was it you?- Aw, man.

– Come on, Elliot, come on, Elliott.

– Elliot, concerning the saxophone, was it you? – (bleep)! – Devlin, is it you? – I have a question.

(all laughing) – Do you play saxophone, but you didn't write that? – I played the saxophone, but I didn't write this one either.

– That's a point, that's a point! (all cheering)- Damn.

– Would the sax man, or woman, please raise their hand.

(all cheering)- wow.

– So, I played the saxophonefrom fourth to fifth grade, and I was terrible.

First I had a reallycute photoshoot with it, and it was adorable.

(upbeat music) – I have competed in 10~ triathlons.

(tense dramatic music) (bleep), who could've done that? I'm gonna guess our forkliftdriving hero, Jonathan.

– I'm gonna go with Rachel.

– I'm gonna go with Kaylin, 'cause I know she ran.

– I'm gonna go with Nick.

I feel like I heard youmention a marathon once, but maybe you were goingto cheer someone on.

– [Miles] Nick, was it you? – Zach, it was me.

(all cheering) – Thanks.

– Hold on, and a hot dog stand? (all cheering) they're very different.

– And a marathon, And a marathon.

– You've done 10, and a marathon? – [Nick] Eight sprintdistance, two Olympic.

– That thrusts Zach intothe lead with two points, and Eugene tailing rightbehind him with one.

– I have the ability to lucid dream.

(tense dramatic music) As in, I can control my dreams.

– We've talked about this, we know that Alexandriahas sleep paralysis.

– Which means she probablydoesn't have lucid dreaming.

(all laughing) You would get out of that situation.

The only person here who Ithink would learn to do it is Miles Bonsignore.

– You know, I'm gonna guess Kaylin.

– I'ma mix it up and say Elliot.

– Elliot, was it you? – So, this wasn't my thing, but I do lucid dream.

– Did I do it again?- Write it down! (all cheering) – Would the owner of a lucid dream please raise your hand.

(all laughing) – So, I was really interestedin it in high school, and I actually made a video about it, 'cause I kinda learned howto do it in high school, and I minored in psychology in college because I was so into it.

– On a technicality, Eugeneclinches a two pointer, bringing him up to three points with Zach, last place being tied at zero points with Ned and Keith.

– I've propelled off the side of a 200-foot tower in Italy.

(tense dramatic music) – [Zach] What does that mean? – [Ned] Does that mean repelled? – No, I believe it says they propelled.

– So, it's someone who's beento Italy, who's adventurous, and also doesn't know the difference between propelled and rappelled.

– One of these has got to be Jonathan.

– I'm gonna go with Elliot.

– Okay, I'm going withsomeone, who I think, is a world traveler, was my initial guess, also seemed super embarrassed about the propelled-rappelled thing, I'm going with Rachel.

– I think Rachel.

It just sounds like something Rachel did.

– Elliot, was it you?(buzzer buzzing) Jonathan, was it you? – No.

(buzzer buzzing) – Rachel, was it you? – No.

(all grunting) – Thought it was Rachel.

– I never make that mistake! – Would the propellerplease raise their hand.

– I was.

(all cheering) – As soon as you said that, my chest started getting hot, and I was like, they'regonna see my red face.

When I was 17, I wentto Europe for a month, and there was a 200-foottower that we rappelled down.

– I had a doppelganger in college, who looked so much like me that people frequentlycalled him by my name.

– So I'm gonna go with Will.

(Keith qcheering) Yee-haw! – 'Cause he literallylooks exactly like me, looks, like, exactly the same.

He has the same face, buthe's, like, more handsome.

– I won a school pageant after lip-syncing “WreckingBall” in underwear, on a workout ball.

This feels slam dunk to me, I'm going Sam.

So you also guess Sam? – I guess Sam.

– Yeah! It was a man pageant fundraiserthat our school was doing, and I was on a workoutball that had a chain, we were swinging, I was in a Speedo.

– In high school, I joined the swim team without knowing how to dive, and had to jump feet-first in the pool for several meets before figuring it out.

Oh, that's so sad.

Oh, this is so sad, Idon't wanna name anybody.

– It was me.

– Elliot! – I didn't realize it was that sad, but.

(all laughing) – I have a titanium shoulderfrom a slackline incident.

– [all] Miles.

– It was me.

– Yeah!- All right! (all cheering) – And into the final round, Eugene and Zach are neck and neck, with seven points andsix points respectively, followed closely by Keith, with just four points, and Ned, tailing behind ata painful two points only.

(upbeat music) – This is a three-pointquestion that Betty White has been a passenger in my car.

(tense dramatic music) Perhaps someone that was, like, a production assistantdriving Betty White around? I'm gonna go for ourproduction assistant, Jonathan.

– I'm gonna rep the Milesnation for this one.

You strike me as a guy that'd be psyched to drive Betty White.

– I think it's eitherNick, Rachel, or Devlin, 'cause Devlin, I know, did a lot of bizarre movie and TV work.

I'm gonna go with Rachel.

– I think it's Nick or Rachel.

I'm gonna go with Nick.

– Nick, was it you? – It was.

– Dang it! Dang it, I knew it! – [Zach] Wow, you're running away with it! – Well, that one I knew, 'cause when it camedown to Nick and Rachel, I was just like, the gaysreally love Betty White.

Like, a lot.

– Correct.

– Yeah, that's something we brag about.

– My Jeep was used as a picture car in a film I worked on called “You Again”, that no one probably remembers, but there's a whole scenewith her riding in my car.

– I defended gay rightson a reality show on TLC, which was called “MissAmerica Reality Check”.

(tense dramatic music) I defended gay rights ona reality show, on TLC, “Miss America Reality Check”.

– Nick!- It's gotta be Nick.

It's just gotta be Nick, because, like– – It's called “Miss America”.

– He defended gay rights, I mean, he could've been– – You think Miss Americawas against gay rights? – You think there wereonly Miss America people as the entire humans on a whole TV show? You don't think therewas a single other person on screen, ever? (all laughing) Not a single one? – Nick, was it you? – It was not.

– Who was it?- Is it Kaylin? – It wasn't me.

– It was Rachel.

– Rachel, finally! Oh, you did do beauty pageant shit! – I was Miss Vermont in 2007, and competed at Miss America in 2008, for which I had to live in a house with the other 52 contestants, and Miss South Dakota was saying only men andwomen should get married, and I went off, and they included it.

(all cheering)- oh yes.

– Let's roll the clip.

(all laughing) – This is a cool fact.

I was once a caterer at EltonJohn's annual Oscar party.

(tense dramatic music) – This is also very gay.

– Yeah.

(all laughing) – Who was in therestaurant industry at all? – I'm guessing Devlin, Ifeel like Devlin's talked about catering as one of his odd jobs.

– Look at how desperate Ned looks.

– This is horrible! Don't like quizzes that Idon't know the answers to.

– I'm going with Miles.

– I'm gonna keep this gay train rolling, I'm gonna say Nick again.

I don't know, it's Elton John! I don't know, I'm hoping it for us.

– It made sense, but Ididn't wanna double dip on that logic.

– Gays love a double dip.

– [Miles] Nick, was it you? – Always bet on gay.

(all cheering)- Thank you.

Thank you.

– I catered in betweenPA jobs back in the day, it was awesome, and then it sucked, because we cleaned up all night long.

– With that dominating performance, Eugene sits atop the leaderboard with an amazing 13 points! The cool boss has emerged victorious, claiming the title of best boss.

(uptempo orchestral jingle) Ned, you fought valiantly, but with only twopoints, that leaves you– – Oh, no! – with the World's Worst Boss mug.

– I don't like this at all! (all laughing) – Keith, we are going to award you with the World's Okayest Boss mug.

– Hey, I think that'sactually pretty true.

(all laughing) – And Zach in second place– – The World's Second Best Boss! You know what, I listen.

– And Eugene, of course, in first place, you are being donned as Best Boss, and being given— Wow! (all cheering) – That's right, let's giveit up for all of our bosses.

– You guys, Eugene loves graphic tees! Put it on, Eugene, come on, put it on! Don't you wanna seehim in the shirt, gang? – [All] Yeah! Boss, boss, boss, boss, boss, boss, boss! Boss, boss, boss, boss, boss, boss, boss! (upbeat rock music) – I know over 200 plus digits of pi.


1415926535897932384626433832795028841971693993 – Pi, pi, pi, pi, pi, pi, pi.

Pi, pi, pi, pi, pi, pi.

Pi, pi, pi, pi, pi, pi, Pi, pi, pi, pi, pi, pi.


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