Bryon (left) and Taylor (right) went head-to-head for pickleball supremacy.
Bryon (left) and Taylor (right) went head-to-head for pickleball supremacy. We're Here To Help

Pickleball showdown settled with advice from 'We're Here To Help' podcast

When Arizona-based pickleball coach, Taylor Osborne, recently needed guidance to solve a moral dilemma, he didn't exactly go the traditional route.

Instead of talking to his better half, a close friend, or a co-worker, he reached out to the We're Here To Help podcast hosted by actor, comedian, writer, and director, Jake Johnson, and stand-up comedian, Gareth Reynolds.

Johnson and Reynolds provide advice to callers seeking answers on a variety of subjects ranging in nature from trivial to serious, and Osborne's issue ultimately proved to be particularly intriguing... because it concerned America's fastest-growing sport.

In Episode 201 (August 27), Osborne explained that his brother-in-law, Bryon, claimed that he would "absolutely destroy" him in a head-to-head pickleball match even though he'd never picked up a paddle in his life.

Osborne, of course, scoffed at that suggestion because teaching the intricacies of pickleball is his livelihood and he obviously knows his way around a court.


"I'm on the fence of do I try and just shut him up and like destroy him and put him in his place? That's nerve-racking because what if I mess up?" Osborne asked Johnson and Reynolds. "And if I don't do that, then what's another way to handle this where I can just be like, 'Dude, this is ridiculous. Like this is what I do. You've never played before. What's the point in us doing this and me embarrassing you in front of the family?' It's just like this weird scenario where I don't know whether to try and take him out or come up with another solution to just try and shut him up."

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The call immediately resonated with Johnson, who's starring in the upcoming pickleball-themed movie The Dink alongside Ben Stiller, Mary Steenburgen, Ed Harris, Chloe Fineman, Patton Oswalt, Chris Parnell, Christine Taylor, Martin Kove, John McEnroe and Andy Roddick.

Some healthy debate ensued before Johnson made his suggestion.

"Here's what I think you have to do, Taylor. You've got to go out there and prove your worth, and if he beats you, maybe kind of a career change," he said. "If you can't beat a guy who has never played and who's talking s%$#... The problem with pickleball is that everybody thinks it's so easy, anyone can do it. The thing that's annoying about it is a 70-year-old lady can pick it up and she's playing just as good as a 24-year-old, but as you and I know, Taylor, there's levels to this game."

There was no turning back after that.

Taylor and Bryon needed to duel in the desert to settle this once and for all.

Johnson and Reynolds proposed a match with family members in attendance to spectate and enjoy the festivities.

"When he serves it underhand and soft, slam it down his a%#," Johnson told Osborne. "And when your wife looks at you like you're being a psycho, go 'This is how I bring food on the table for us.' This ain't a game."

Before any formal arrangements were made, however, Bryon joined the podcast to share his perspective on the situation.

And he was brimming with confidence.

"I will annihilate him," he said. "I played tennis. I played ping-pong. I'm pretty sure I will be alright."

"I find this whole conversation insane. There's no way I don't take the win," replied Osborne with a laugh. "I think he might score a few points when I mess up, but outside of that, I think basically I'm only going to need two games and it'll be over after that."

The match (best of three games) was finally scheduled for Friday, September 19th.

As for the stakes involved, the loser would be required to serve a family dinner wearing an elephant trunk Speedo and openly admit the winner is the better pickleball player.

"This is the sporting event of the year," mentioned Johnson. "This is the We're Here To Help Super Bowl. This is our first Super Bowl."

The showdown, which featured announcers on-site, was recorded, and a YouTube video was compiled as well.

So who won the first-ever Pickle and Chip Classic? Watch and find out.


To learn more about the lead-up to the match, listen to Episode 210.

To hear Taylor's thoughts on the match, listen to Episode 212.