5 Ads for a Reason: Thank You Rico Bosco

All this week, the focus has been on Jeff Nadu, with people like Big Cat and other Stoolies acting like he’s the king of content and some mastermind. Nadu is even telling Rico he’s only funny when the joke is about himself, Jeff Nadu. That’s just false. There’s only one man who has been co-hosting a podcast across multiple presidencies and consistently rakes in five ads per episode. That man is Rico Bosco, and that podcast is Barstool Pick ‘Em.

Now, yes, Dave and Big Cat, two huge media personalities, are also on the pod, but as producer Hank once said, "Rico is the straw that stirs the drink". He’s the reason people come back week after week. Anyone can do a picks show, but nobody, and I mean nobody, has what Rico has. And frankly, it can’t be replicated either. Pick ‘Em is my favorite podcast. It was the first piece of Barstool content I ever heard after seeing a clip on Twitter during COVID. So for my rankings, I’m covering the years 2019 through 2024, since I’ve listened to all of those shows multiple times.

What follows are 10 moments that always make me laugh, no matter what. Cutting this l*st down to ten was insanely hard, but every single one of these moments has one thing in common: Rico Bosco.

2022 – Return of RB

Now, this isn’t one of my favorite episodes, but it has to make the rankings. Mainly because Pick 'Em is great because of Rico, and his return saved the best show Barstool produces.

Yes, it was a squeeze-out. Yes, it was a small mistake by Bosco. But it was still a legendary moment when Mount Rydermore got rebuilt.

2020 Week 14 – "Whore"

2020 was a huge year for Pick 'Em, especially for Rico Bosco. After staying anonymous in previous seasons, he stepped into the spotlight as a full-time employee and finally showed up on camera. That move paved the way for Bench Mob, a great college basketball podcast that

was honestly ahead of its time.

But success breeds jealousy, and Jeff Nadu couldn’t help himself. He wormed his way into Dave and Big Cat’s orbit and tried to create confusion between his garbage podcast and Rico’s ad-generating machine. Around Black Friday, mockery merch dropped targeted at Rico, and Dave absolutely knew about it. That created one of the most hostile (yet hilarious) openings in Pick 'Em history, where Rico calmly explained he was being used like a whore. Dave, of course, ran with that. Then Hank and Big Cat deliver one of the funniest exchanges ever, where Hank,#1 Ryder, coins the term “Hot and Cold Cat”. It all just proves again: Rico’s reaction to these skell antics is what makes the show great.

2021 Week 11

The 2021 season was absolutely legendary, and this episode is evidence of that. The Mortal Lock Parlay was at its peak, and “relegation” had been introduced; if your Mortal Lock missed three weeks in a row, you were out. Rico, being the honorable man he is, pointed out that Big Cat had also lost three straight. But of course, due to anti-Rico bias, his picks were tracked with laser precision, while Dan’s losses got conveniently swept under the rug.

Rather than take his lumps, Big Cat decided to go full Nadu Fetish Mode and wanted to replace himself with a man who didn’t even work at Barstool at the time. Again, classic Pledge Master Dan trying to rattle Rico. There are a ton of funny moments in this one, but the best clip is Rico casually calling it out while Dan gets all pissy.

2019 Weeks 13/14

The original skells might not be known to newer Stoolies, but let me educate you: back in 2019, there were three primary villains: the Cowboy (yes, the one who wore the hat at Luger's), Big T, and Captain Cons, who came in like a third-string QB piling on. They made mockery merch calling Rico "Soft Serve Ice Cream" in Week 14. This stemmed from Cons falsely accusing Rico of giving out La Tech, which he did not , resulting in a legendary Rico explosion.

Dave and Dan, being on-the-fence Ryders at the time, even flirted with joining the Wolfpack (the Cowboy’s group), tweeting out his handle to help him get more followers than Rico. Classic skell behavior. Dave was dialed in during this stretch too. He wasn’t just watching one game, he was watching everything. He lost around $500K between Michigan and Wisconsin in a few hours, betting every game on the board. That was peak Dave ball knowledge, and I miss it.

2021/2022 – March Madness Round of 64

This episode set the tone for the 2022 season, which was by far the most hostile Pick 'Em year, thanks to contract drama and Rico’s college basketball ban. Rico had built legit connections with players like Luka Garza and Cade Cunningham. For some reason, Dave had a major issue with how Rico talked about "his guys," and that sparked a 30-minute shouting match between the three. Rico goes off on a legendary tangent. Then, once they finally start making picks, it turns into a hilarious bracket pick 'em and over/under segment. Just an elite episode from top to bottom.

2019 Week 7

As a Ryder, I denounce the Rico slander in this episode, but the dynamic between the Big Three is on full display. The show opens with them talking about their “Positive Vibes Only” merch, a phrase Rico had been using since multiple presidencies ago, yet he still didn’t get a hat or credit.

Then Hank reveals Rico soft-blocked him on Twitter, which creates tension between the two Ryders. Later, Rico brings in some prosciutto and mozzarella, not knowing it was Yom Kippur.

Dave, of course, saw the angle and went full Skell Pres, accusing Rico of being anti-Semitic. That led to a whole Merry Christmas/Happy Hanukkah debate, and somehow, Rico gets compared to the H man.

Oh, and let’s not forget: this is the infamous 12-unit Toledo play episode. More on that later.

2020 Week 8

If you’re a real Ryder, you know there are only a few original guys left, and one of them is Sully Soprano. To my knowledge, he’s the only Hype Circle guy still consistently active.

Back then, Rico had a Ryder group chat with top-tier Twitter Ryders. They mostly played survival pool and Name That Tune, but occasionally vented or organized skell takedowns.

In the heat of an argument, Rico accidentally hinted that this group existed. Blood in the water. Dave and Big Cat immediately forced their way in, exposing the inner workings of Rico’s mind and the Ryder defense system.

The fallout is hysterical and unique. This ain’t your average picks show. This is Pick ‘Em.

2019 – Toledo Week

This one’s a classic. “Burger” was a term Dave and Dan used for bad picks that Rico made.

Rico gave out Toledo as a massive favorite… and they lost outright. His reason? The coin toss. A truly hilarious moment when Dave and Dan realize what he said. Rico, realizing the room is against him, talks about one of the funniest stories that honestly has a good life meaning. Meanwhile, Glenny Balls is in the background actually making burgers while Rico gets yelled at for going dark after the game and letting Hank down. It ends with Rico eating a burger on camera to put the bit to rest.

One of the most ridiculous and entertaining episodes ever.

2022 – Whitney Week

Second place goes to Whitney Week. Ryan Whitney, a Ryder, though his Nadu-related behavior and coaching KMS are questionable lately, joins to help sort out the chaos in 2022.

At this point in 2022, it didn’t look like Rico would be extended. The blog rankings were a major issue, and vibes were at an all-time low. Rico had been on The Dave Portnoy Show a bunch, and things were spiraling.

They basically hold a Ryder Roundtable to figure it out. Dave makes a snide comment about the "narratives in Rico’s head," which leads to an all-time blow-up. Whitney jumps in, calling out Dave and Dan for constantly running hit pieces about Rico joining the Taliban (he’s not) and committing tax fraud (he didn’t). The first 30-40 minutes are pure gold.

2021 Week 1 – Contract Negotiations

Number one. No debate. This is the GOAT episode. It’s also the most viewed video on the Barstool Gambling page for a reason.

Rico doesn’t have a new deal, so he opens the episode by announcing a holdout. Dave immediately tries to negotiate with Big Cat, playing the middleman. For 50 minutes, they go back and forth on numbers, years, “ziti and sauce,” all the key terms. Then, it gets revealed that Rico was already making more than Dave thought.

Being the stand-up guy he is, Rico made sure to hit the ground running when the new contract came in the previous year. Dave loses it. He tries to box Rico into an auto-renew deal. Then the legendary timeout scene happens. Eventually, they figure it out. Rico, emotional, wraps a cord around his neck like a collar and says: “I should wear this, since you’re fucking me.”

It’s a Hall of Fame moment. Mandatory viewing for any real Stoolie.

Final Thoughts

Pick ‘Em is hilarious, always has been, always will be. Even the episodes not on this l*st are gold and make for a perfect, relaxed take on college football.

Rico is one of a kind. He makes the show dynamic. Hopefully, Dave can get more locked into the games like he used to for the 2025 season.

And finally, shoutout to Kenny Hammer and Derrick from the chat for helping me put this together.