Funniest Bad Friends Guest Appearances

The comedy podcast Bad Friends, hosted by Bobby Lee and Andrew Santino, has been on a roll, delivering episodes packed with laughs and chaos. With surprise guest appearances from comedy heavyweights like Bill Burr and a revolving door of hilarious personalities, it’s clear this year has been one for the books.

Here’s a recap of the most memorable guest moments from the last nine appearances, where the chemistry and spontaneity reached peak hilarity.

Bill Burr’s Surprise Drop-In

Bill Burr’s unannounced visit caught everyone off guard—and not just because of his comedic chops. Bobby couldn’t help but marvel at the randomness of seeing Burr outside their usual haunts:

“We see each other at The Store all the time, but now you’re acting like you flew in from New Zealand!”

The riffing quickly turned into a comedic roast of their shared history, proving that even seasoned comedians can’t escape Bad Friends’ signature chaos.

Donnell Rawlings Clears the Air (Or Tries To)

Donnell Rawlings brought his unfiltered energy to the show and immediately had to address some wild internet rumors:

“Diddy is NOT my boy!”

Of course, Santino and Lee weren’t about to let him off the hook, hilariously “fact-checking” his claim with Photoshopped images of him partying alongside P. Diddy and Magic Johnson. The laughs escalated as Rawlings tried to steer the conversation back to reality but failed gloriously.

Bobby’s Wild Tangents: Tyler Phillips and Football

No Bad Friends episode is complete without Bobby Lee launching into a story that seemingly has no connection to the topic at hand. While discussing football, Bobby veered into a tale about his childhood friend Tyler Phillips, who had a missing eye:

“He’d sleep on his side, but the empty eye socket would stay open. Freaked me out, man!”

It’s these bizarre asides that make Bobby a comedic wildcard, leaving both Santino and the audience in stitches.

Bobby Lee Gets Roasted Over “Curb” Appearance

When Bobby’s role in Curb Your Enthusiasm came up, Andrew couldn’t resist teasing him:

“That doesn’t even look like you! It’s either you or Joe Koy!”

The exchange turned into a laugh-out-loud debate over Bobby’s evolving look and acting choices, with Bobby demanding credit for his performance while enduring Andrew’s relentless ribbing.

Theo Von’s Wisdom and Tyler’s Dad’s Box Seats

Theo Von also made an appearance, contributing his signature brand of offbeat wisdom. The hosts recounted hilarious memories, like attending a Vikings game in box seats courtesy of Bobby’s friend’s dad:

“My dad fell asleep the entire time. Embarrassing, but he needed the rest!”

The blend of heartwarming anecdotes and absurd humor hit all the right notes, embodying Bad Friends’ unique tone.

A Tangent-Heavy Dynamic That Works

Beyond the guest appearances, Bad Friends thrives on the chemistry between Bobby and Andrew. Whether they’re roasting each other, breaking into improvised tongue twisters, or unraveling absurd debates (is Gaza a road?), the podcast proves that the best comedy often emerges from sheer unpredictability.

Why Guests Keep Coming Back

With its mix of off-the-wall storytelling and razor-sharp wit, Bad Friends has become a favorite for comedians and fans alike. Whether it’s exploring bizarre tangents or welcoming surprise guests, every episode feels like a party you’re thrilled to crash.