3 Times Bert Kreischer Got Hilariously Roasted by Fellow Comedians

Bert Kreischer might be one of the funniest guys in comedy, but that doesn’t mean his friends won’t roast him every chance they get. Here are three times fellow comedians hilariously ripped into him.

1. Shane Gillis on Bert’s Singing

Bert tried his hand at singing “Wagon Wheel” and Shane Gillis had just one reaction: “What do you think? [ __ ] gay.” Short, brutal, and exactly what you'd expect from Shane.

2. Neil Brennan’s AI Bert on Two Bears, One Cave

Neil Brennan created an AI version of Bert, and it was painfully accurate. The bot kept derailing conversations, forcing everything back to Bert, and even generated a fake story about his daughter Georgia—just like real-life Bert. “This sucks! Make this about Bert!” The machine truly captured The Machine.

3. Big Jay Oakerson’s Perfect Bert Impression

Big Jay nailed Bert’s signature storytelling style: take off his shirt, exaggerate a situation, then drop the classic line—“And I says… she says… wa she go…” If you’ve seen a Bert special, you know this is spot on.

Bert gets roasted, but let’s be honest—he loves every second of it.