Podcasts by What Should We Draw

What Should We Draw

The show where we use the art of conversation to make art ABOUT a conversation!

Further podcasts by Headgum

Podcast on the topic Comedy

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What Should We Draw
Episode 2: Cat Regatta (w/ Hallie Cantor) from 2022-02-21T02:28:57.747228

Ahoy friends! Welcome aboard episode 2 of our podcast! On this week's nautically-charged adventure we're joined by writer and Diet Sunkist spokeswoman, Hallie Cantor (Inside Amy Schumer, The New Yo...

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What Should We Draw
Episode 3: Mystery Class (w/ Jake and Amir) from 2022-02-21T02:28:57.743526

Welcome to FUCK COURT, where the only crime is not being sexy enough! Oh, and arson. Definitely arson. In this extra sexy episode, Caldwell and Nathan are joined by Headgum Founders Jake Hurwitz an...

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What Should We Draw
Episode 7: #NONTENT (w/ Jacob Andrews) from 2022-02-21T02:28:57.728149

Hey, it’s us. Your real podcast hosts. Don’t look in that closet. Ignore those screams. C’mon! It’s your old pals Cardwall and Nayfin. You can trust us. On this episode we’re joined by our illustra...

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What Should We Draw
Episode 11: Hogsports (w/ Siobhan Thompson) from 2022-02-21T02:28:57.682715

If you’re listening to this episode, it means you’ve been officially selected to join the 2017 class of incoming freshman at Dumb Hogwarts School of Bad Magic and Hecked Up Spells. Congratulations!...

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What Should We Draw
Episode 15: Wearable Cars (w/ Tony Wilson) from 2022-02-21T02:28:57.672082

Welcome to Caldwell's comic basement AKA your one-stop shop for cutting edge smell and touch-only comic experiences. That's right, four panels, four senses. No seeing, NO PROBLEM. Oh, wait. What's ...

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What Should We Draw
Episode 16: Absolute Kevin (w/ Pat Wise) from 2022-02-21T02:28:57.670929

Before you begin listening to this week's episode we must warn you, it contains dark truths. What began as an innocent conversation between Caldwell, Nathan and comedian Pat Wise (the creator of th...

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What Should We Draw
Episode 20: CUBE (w/ Adam Conover) from 2022-02-21T02:28:57.659272

On today’s episode of What Should We Draw, Caldwell and Nathan get put on PODCAST BLAST by their guest Adam Conover (TruTV’s Adam Ruins Everything), who hijacks the show to talk at length about cub...

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What Should We Draw
Episode 24: Have Some Dogs (w/ Andy Stuart) from 2022-02-21T02:28:57.581219

ALL RISE FOR THE HONORABLE KING BUFF KING NATHAN AND HIS ESTEEMED COLLEAGUE KING BURGER KING CALDWELL. Today our two Artistic Arch-monarchs welcome into their court Lord Andy “Noob The Loser” Stuar...

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What Should We Draw
Episode 35: Number by Colors from 2022-02-21T02:28:57.569159

Hey there friends. Boy, it sure has been a stressful 24 hours, huh? Just to let you guys know, we recorded this episode a while ago and we did not address any current events. So, if you want a litt...

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What Should We Draw
Episode 37: Magical Mikes and Where to Find Them (w/ Cynthia Kao) from 2022-02-21T02:28:57.567179

Oh boy, this here is a good and not bad podcast episode for you yes! On this week's show, Cynthia Kao (Collegehumor Originals, Adam Ruins Everything) joins our hosts as they prepare to launch their...

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What Should We Draw
Episode 41: Slug Buddies (w/ Sarah Andersen) from 2022-02-21T02:28:57.486124

Caldwell and Nathan invite webcomic artist extraordinaire Sarah Andersen (sarahcandersen.com) to help them develop some hot new products ranging from sticker mods for money to engraved swords for m...

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What Should We Draw
Episode 44: Goop Dreams from 2022-02-21T02:28:57.483274

Oops! Caldwell and Nathan forgot to start the episode and ended up just talking about goo for 50 minutes. I guess they figured that they could just post that sticky conversation and hope no one not...

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What Should We Draw
Episode 47: Red, White and GRU from 2022-02-21T02:28:57.476799

Howdy y'all and welcome to the Nathan Farms! It's a nice, chill place where all Nathans can come and roam free. We've got Smash Brothers over by the barn, Wet Bread Ale on tap, and nightly showings...

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What Should We Draw
Episode 53: Assume No Caldwells (w/ Jacob Andrews) from 2022-02-21T02:28:57.461349

Nathan is having a stress nightmare. It's podcast exam day and not only did he forget to study, he left his Caldwell at home! Luckily, former guest/amazing cartoonist/good friend Jacob Andrews is h...

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What Should We Draw
Episode 59: Caldwell and Nate PLUS KATE from 2022-02-21T02:28:57.447259

Today's historic episode of WSWD celebrates the stunning ingenuity of Kate S, who sent in not one, not two but THREE amazing drawing suggestions. Inspired by Kate's generous offerings, Caldwell and...

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What Should We Draw
Episode 66: The Call-Out King from 2022-02-21T02:28:57.372017

Hear ye! Hear ye! It is I, the Podcast King, here to call out this episode of What Should We Draw. Hosts Caldwell and Nathan are in BIG TROUBLE for making such a nonsensical and silly episode. What...

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What Should We Draw
Episode 68: Spider Cider from 2022-02-21T02:28:57.368490

Caldwell and Nathan are fully spider on this episode of What Should We Draw. Join these two arachnophiles as they spin a conversational web through topics such as infinite menorah glitches, strong ...

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What Should We Draw
Episode 70: My God Damb States from 2022-02-21T02:28:57.357422

It's the GOD DAMB New Year and whether you are looking for new things to text your friends, attempting to deal with a sick turtle, or simply trying to make your home state seem more cool, Caldwell ...

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What Should We Draw
Episode 61: Dad Island from 2021-01-31T22:10:42.023393

Welcome friends... to Dad Island, a magical place where fathers can roam free, unhindered by the constraints of modern life. Today, Caldwell and Nathan have ventured to this mythical papadise for a...

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What Should We Draw
Episode 74: Ear Loaf from 2018-02-28T18:23:39

Hope your ears are hungry because Caldwell and Nathan have cooked up a tasty loaf of content on this episode of What Should We Draw. Allow your hear-holes to savor the flavors of topics such as CGI...

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What Should We Draw
Episode 73: The One True Nipple (w/ Trevor Lyon) from 2018-02-14T21:18:42

Caldwell and Nathan invite their editor Trevor Lyon to step out from the shadows and join them for a riveting conversation about new units of measurement, casting calls for food, and consensual hug...

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What Should We Draw
Episode 72: YEET from 2018-01-31T21:07:07

The Drawboys are back and they're ready to yeet out another sweet yeeting podcast episode for all the precious little yeetlings out there in Listener-land! This week on the show, Caldwell and Natha...

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What Should We Draw
Episode 71: Spice Idiot from 2018-01-17T21:28:46

Caldwell and Nathan invite you to join them as they venture deep into the snowy forest that is their inbox in search of noteworthy emails to answer on this episode of What Should We Draw. Topics in...

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What Should We Draw
Episode 69: "It's a Table" (w/ Tony Wilson) from 2017-12-20T19:10:17

It's here. We finally made it. The Nice Number. The Sensual Digit. The horny ordinal itself, EPISODE SIXTY-NINE. To celebrate, Caldwell and Nathan went out for drinks with their good friend Tony Wi...

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What Should We Draw
Episode 67: THRURTLE from 2017-11-22T18:36:25

Y'all, this episode has it ALL. Cat stories. Bible Tales. ROBOT VOICES. It's a literal pre-thanksgiving FEAST. So please, revel in the bounty of a new podcast, but be wary, for the Wicked Coalition...

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What Should We Draw
Episode 65: Curse of the Silver Mummy from 2017-10-25T19:59:53

Happy Almost-Christmas! Let us raise our mugs of eggnog and celebrate this day of victory, for the War on Christmas is won, and soon the Jolly Times shall be upon us. Until that day though, Caldwel...

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What Should We Draw
Episode 64: My Morning Grotto (w/ Murph and Emily) from 2017-10-11T15:47:23

The Dog Days of Summer are here at last! Nathan's out of town, so Caldwell recruits Murph and Emily (POPTV's "Hot Date") deep into his morning grotto for a breakfast-time chat about orcs, hyper-loc...

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What Should We Draw
Episode 63: Swimless Fish from 2017-09-27T18:55:33

Caldwell joins Nathan in the space between for a sleepy conversation on this episode of What Should We Draw. Join our tired travelers aboard their rogue mower as they tour the nation searching for ...

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What Should We Draw
Episode 62: Teen Christmas (w/ Dan Hopper) from 2017-09-13T18:17:03

Caldwell, Nathan and special guest Dan Hopper (CollegeHumor, Cracked.com) invite you to enjoy this hour-long audio meme. Don't worry, this gigantic meme is jam packed with smaller conversation topi...

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What Should We Draw
Episode 60: What Should We Smell from 2017-08-16T18:09:22

You smell that? It's a piping hot new podcast episode full of tantalizing olfactory sensations just for you. Join Caldwell and Nathan as they lead you by the nose through a lovingly curated menu of...

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What Should We Draw
Episode 58: Yoshi's Yarmulke from 2017-07-26T17:25:48

Caldwell is sick on this episode of What Should We Draw so rather than coming up with a drawing idea, he and Nathan spend a good chuck of the show discussing Valerian and the City of a Thousand Pla...

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What Should We Draw
Episode 57: The Yummy Chair from 2017-07-20T15:25:25

Caldwell and Nathan are starting a new school this year and they want to make the very best of impressions. As such, they’ve decided to change both their names AND the name of the podcast. So witho...

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What Should We Draw
Episode 56: Wrong-a-Dong (w/ Monica Ray) from 2017-07-12T16:10:53

Fear not listeners! The WSWD HERO SQUAD has arrived to save you from the terrors of boredom. Today, top-tier heroes Pasta Friend and The Snoozer are joined by Monica Ray (Disney) AKA THE MONIKER fo...

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What Should We Draw
Episode 55: Strife Alert (w/ Jeff and Dave Rosenberg) from 2017-06-28T23:14:27

We know that all episodes of What Should We Draw have an explicit content warning but it applies double for this one. In fact, everything on this episode has been doubled including the number of gu...

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What Should We Draw
Episode 54: Garfgate (w/ Willie Muse) from 2017-06-21T18:21:31

The #TeamWillie Nation has spoken! Once again Caldwell and Nathan are joined by the Prince of All Scamps, Willie Binder-Flannel Muse (CollegeHumor) for a discussion about augmented lasagna apps, Wi...

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What Should We Draw
Episode 52: The Mouthman Prophecies from 2017-05-31T20:50:06

Move over eyes! Mouths are the new windows to the soul. Whether they are slapping the dicks out of them, filling them with Shakespearean insults or simply enjoying their beauty, our hosts just can'...

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What Should We Draw
Episode 51: Mixed Malaphors (w/ Shea Strauss) from 2017-05-17T08:06:17

Today's episode of What Should We Draw is almost exclusively concerned with the devilish art of the malaphor. For the next 57 minutes, Caldwell, Nathan and special guest Shea Strauss (CollegeHumor)...

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What Should We Draw
Episode 50: REDEMPTION from 2017-05-10T19:12:03

We hope you are looking forward to looking backward! To celebrate reaching their 50 episode milestone, Caldwell and Nathan take a trip down memory lane and revisit some of their favorite ideas from...

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What Should We Draw
Episode 49: The Bosch Button from 2017-04-26T16:35:17

WARNING: This podcast episode is for BOSCH FANS ONLY. If you’re not a hardcore Boscha-Nova, then you can just Bosch right off, ‘cause on this episode we’re talking’ about nothin’ but Bosch, baby! W...

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What Should We Draw
Episode 48: Blood Uncles (w/ Emily Bogue) from 2017-04-19T18:57

Check! Check! Is this thing on? Your headliners, The Blood Uncles, will be out shortly but first we've got an opening act you're really gonna like. It's Caldwell and Nathan featuring Emily Bogue (A...

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What Should We Draw
Episode 46: Rice Advice (w/ Jillian Vogel) from 2017-03-29T18:10:45

Greetings constituents! It is I, Omni-Mayor, welcoming you to a very exciting episode of What Should We Draw. After all, it is the episode during which I was birthed. Caldwell, Nathan and Jillian V...

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What Should We Draw
Episode 45: Cow Court (w/ Bria Jones) from 2017-03-15T17:35:57

Today's WSWD is a TRIAL BY PODCAST. Special guest judge Bria Jones (Animator, Bob's Burgers) presides as Caldwell and Nathan engage in civic discourse over the quandaries that have rocked our natio...

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What Should We Draw
Episode 43: Pay-Per-Moon (w/ Cheyenne Curtis) from 2017-02-23T19:42:20

Hey roomie, did you get my note? The one embroidered on that huge spider's web next to the fridge? About not drinking my milk? Oh you didn't? Because you were too busy listening to the latest What ...

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What Should We Draw
Episode 42: Befuddle the Duddles from 2017-02-15T18:27:22

This week’s episode of What Should We Draw is all about TRYING NEW THINGS. Join Nathan and Caldwell as they plunge deep into their newly expanded comfort zones for a rousing conversation about the ...

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What Should We Draw
Episode 40: Sven the Swaddler from 2017-01-18T21:28

ALL ABOARD THE COZY TRAIN. On this week’s episode of What Should We Draw, Caldwell and Nathan use the Danish philosophy of hygge to prepare an incredibly soothing audio experience designed to put y...

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What Should We Draw
Episode 39: Hep to the Zep (w/ Julia Lepetit) from 2017-01-11T20:52:03

Caldwell and Nathan invited former guest, Julia Lepetit (Dorkly.com), to help them rummage through their mailbag in this first episode of the new year. Join our hosts in their conversation dirigibl...

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What Should We Draw
Episode 38: Bad. Of the Bone (w/ Magnolia Porter) from 2016-12-22T05:51:53

Gather close, Young Riders. Gather close and listen well. For today, from the Whispering Void known only as What Should We Draw, comes a tale of speed, avarice, and several very beefy, bald men. Cl...

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What Should We Draw
Episode 36: The Truth About Beans (w/ Rekha Shankar) from 2016-11-23T08:48:56

Greetings from the vaulted depths of our spacious podcast manor! On this week’s show, Caldwell and Nathan sit down between their two baby grand pianos to chat with comedian and writer Rekha Shankar...

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What Should We Draw
Episode 34: Apple-tizers from 2016-10-26T18:32:04

Hello Friend! Are you ready to Have Make Amazing opportunity? All you need do is Listen to New Episode of What Should We Drawing for exciting Business Insider Tips! Caldwell and Nathan (the Very Dr...

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What Should We Draw
Episode 33: The Basement from 2016-10-19T20:29:09

My dearest child, I beseech you hear the tale of Caldwell and Nathan and horror they unleashed from below. This episode of What Should We Draw is a warning to all curious children who seek to know ...

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What Should We Draw
Episode 32: Sleight of Ham (w/ Zach Weinersmith) from 2016-10-12T17:12:05

If you’re listening to this episode of the podcast and your name is Justin Pierre James Trudeau. FUCK YOU. Put on a goddamn shirt and come fight us this instant. If you’re name ISN’T Justin Pierre ...

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What Should We Draw
Episode 31: Souprise! (w/ Pat Cassels) from 2016-09-30T15:00:29

Well howdy y’all! Welcome to the Souplantation! We sure wasn’t expecting no visitors, but since y’all’s here, we might as well sit for a spell and have a bowl of my grandpappy’s famous corn chowder...

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What Should We Draw
Episode 30: SNEATH from 2016-09-21T16:35:10

On this week’s episode of What Should We Draw, Caldwell and Nathan are joined by an Invisible Sense of Constant Dread ( Last Comic Standing, Funny or Die) for a conversation about Tree Crime, the E...

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What Should We Draw
Episode 29: Tank in a Tank (w/ Jon Gabrus) from 2016-09-14T18:23:42

Sorry DPS and Healer classes, this week’s episode of WSWD is all about Tanks! Joined by the legendary Tank in a Tank himself, Jon Gabrus (High and Mighty Podcast), Caldwell and Nathan embark on an ...

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What Should We Draw
Episode 28: Rollst Beef (w/ Josh Ruben) from 2016-08-31T16:03:50

It's another Michael Douglas morning here at WSWD studios, and to help celebrate Caldwell and Nathan have invited hyper-talented actor and director Josh Ruben (The Mindhouse Podcast) to join in the...

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What Should We Draw
Episode 27: A Farewell to Cargs from 2016-08-24T18:20:46

This week's episode takes a more somber tone than usual as Caldwell and Nathan say their goodbyes to the article of clothing that defined their childhoods. Our two hosts turn to Twitter to help eas...

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What Should We Draw
Episode 26: FlossTalk (w/ Katie Marovitch) from 2016-08-17T08:12:04

Welcome back, flosskateers! It's time for another exciting, ultra-hygenic episode of everyone's dentist's favorite floss-based podcast, FLOSSTALK! Today on the show, Caldwell and Nathan chat with p...

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What Should We Draw
Episode 25: Lil' Battle Boys (w/ Zac Oyama) from 2016-08-10T20:13:56

Caldwell and Nathan try putting a little zoom on their podcast this week as they invite Zac Oyama (CollegeHumor Originals) to have an extra spicy chat about hot sauce, Satan, dad totems and the new...

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What Should We Draw
Episode 23: Duplassity (w/ Willie Muse) from 2016-07-27T23:20:15

Greetings sportsfans! On today’s episode of What Should We Draw, Caldwell and Nathan are joined by Foodball enthusiast Willie Muse (CollegeHumor) for an extended chat about postmodern ninja turtles...

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What Should We Draw
Episode 22: Parkour Horse Course from 2016-07-20T16:25:08

With no guest to occupy them, Caldwell and Nathan once again turn to their beloved audience for inspiration on this week's episode. Our two hosts discuss America's founding uncles, horse pranks, cr...

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What Should We Draw
Episode 21: Czar Talk (w/ Lindsay and Alex Small-Butera) from 2016-07-13T22:57:08

Time to stop worrying and learn to love the Truth Bomb, because on this week's episode of What Should We Draw, Caldwell, Nathan, and guests Lindsay and Alex (Baman Piderman, Adventure Time) are ven...

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What Should We Draw
Episode 19: Big Pool of Pukwudgie (w/ Brian Murphy) from 2016-06-29T19:31:33

This episode goes out to all the dudes, fellas, chaps, lads, blokes and human women with actual names out there just CRUSHIN' it on the DAILY. Today on What Should We Draw, Caldwell and Nathan are ...

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What Should We Draw
Episode 18: Dad Marriage from 2016-06-22T22:52:34

Today’s episode of What Should We Draw is nothing less than a belated Father’s Day miracle. After officially daduating from Father College, Caldwell and Nathan dive head first into the sweltering d...

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What Should We Draw
Episode 17: Pleasure Hell (w/ Julia Lepetit) from 2016-06-16T21:25:45

Fun Fact: Today’s episode of What Should We Draw is actually the first in a long line of commissions from our newest sponsor, The Medici family! In order to handle their generous benefactor’s multi...

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What Should We Draw
Episode 14: Wetbox (w/ Mike Trapp) from 2016-05-25T18:29:14

This week’s episode of What Should We Draw is brought to you by our first and only sponsor, WetBox! If you’re craving a slippery substance and don’t have time for cups, then Wetbox is for you! On ...

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What Should We Draw
Episode 13: Duck Week from 2016-05-18T18:31:27

Welcome to the pilot episode of Past Friends, our new pop-up historical podcast that we tricked you into subscribing to! In this deeply enriching episode, we discuss the invention of pasta, waterfo...

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What Should We Draw
Episode 12: Nickelback ORIGINS (w/ Terence Wiggins) from 2016-05-11T20:12:39

We can proudly say with 100% certainty that the episode of What Should We Draw you’re about to hear is the greatest version of the program to exist across the known multiverse. Several lesser versi...

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What Should We Draw
Episode 10: LizardTube from 2016-04-27T20:48:23

On their first GUEST-FREE episode, Caldwell and Nathan invite YOU the LISTENER into the studio for a rollicking dip into the WSWD mailbag. That's right! All the topics they discuss in this episode,...

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What Should We Draw
Episode 9: Bully Tech (w/ Streeter Seidell) from 2016-04-20T16:18:31

Great news, gang. We just signed a HUGE deal with one of Silicon Valley's hottest new startups, and as a result, all future episodes of What Should We Draw are going to be posted EXCLUSIVELY to SKW...

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What Should We Draw
Episode 8: SnapChateau (w/ Lisa Hanawalt) from 2016-04-13T20:02:59

Today's episode of What Should We Draw was recorded LIVE aboard our brand new boat! We named it "Daddy's Little Secret" after our recently deceased horse. He died after falling off a cliff while ta...

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What Should We Draw
Episode 6: Art Jail (w/ Susanna Wolff) from 2016-03-30T19:04:06

Well, we had a good run, gang, but unfortunately our numerous crimes against creativity have landed us in maximum security art prison. Luckily, they let us keep our recording equipment. In this epi...

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What Should We Draw
Episode 5: Ultimate Fidgets (w/ Jeff Rubin) from 2016-03-23T18:56:15

Hey, can you guys keep a secret? How about roughly 200 of them? Okay, that’s good to hear, because this episode is crammed to the teeth with all sorts of high-level, black market secrets you just c...

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What Should We Draw
Episode 4: Always a Little Wet (w/ Emily Axford) from 2016-03-16T07:57

On this week's episode, Caldwell and Nathan prove that dreams really do come true by giving their friend Emily Axford (Adam Ruins Everything, CollegeHumor) a complete personal brand makeover. They ...

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What Should We Draw
Episode 1: Impossible Pectorals (w/ Jake Young) from 2016-02-22T20:15:50

Welcome to What Should We Draw! The show where we use the art of conversation to make art ABOUT a conversation! In our initial episode, Nathan and Caldwell are joined by Wandering Nerd Warrior J...

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What Should We Draw
Episode 1: Impossible Pectorals (w/ Jake Young) from 2016-02-22T20:15:50

Welcome to What Should We Draw! The show where we use the art of conversation to make art ABOUT a conversation! In our initial episode, Nathan and Caldwell are joined by Wandering Nerd Warrior J...

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