Discover2 Bears, 1 Cave with Tom Segura & Bert KreischerEp. 96 | 2 Bears 1 Cave w/ Tom Segura & Roy Wood Jr.
Ep. 96 | 2 Bears 1 Cave w/ Tom Segura & Roy Wood Jr.

Ep. 96 | 2 Bears 1 Cave w/ Tom Segura & Roy Wood Jr.

Update: 2021-08-3021


- Go to and use code BEARS at checkout to receive 5% off your order
- Go to to try it for FREE when you use our promo code BEARS at checkout and just pay $5 shipping.
- Go to and enter promo code BEARSVIP to get 15% off
- Get your Bud Light Retro Summer Tie Dye Variety Pack at or pick it up at your local neighborhood grocery, convenience or liquor store
- Go to and use the code CAVE to get a 60 day free trial
- Check out and receive 10% off your first order by using the code CAVE
- Download the DraftKings app NOW and use code BEARS to get a FREE shot at MILLIONS of DOLLARS in prizes with your first deposit!

Bert Kreischer is out for this episode of 2 Bears, 1 Cave, but Roy Wood Jr. joins Tom Segura in his place. Roy and Tom talk about Roy's podcast "Roy's Job Fair" in which he interviews people with interesting jobs. This leads Roy to discuss the various jobs he had when he was young, including one where he worked in a hospital kitchen with a man who was stealing pills from the patients. Roy also discusses getting arrested, and working at Golden Corral while he was on probation. Tom and Roy also talk about cancel culture, Shane Gillis being fired from SNL, Janet Jackson's Super Bowl nip slip, and the times Roy got suspended on terrestrial radio. Roy recounts his experience taking over for Ari Shaffir as the host of "This Is Not Happening," and the backlash Ari got for his Kobe Bryant tweet. Tom and Roy wrap up by discussing airplane etiquette, and the time Roy accidentally played an "adult video" on a plane.

Comments (9)

Me Him

What a fuckin yawn fest that was, he has the most depressing voice I've ever heard

Oct 6th

Michael Reznor

the guy who said the n word at that meeting was quoting someone else. someone else used that word and didn't get any flack for it so he was using the word to show the double standard

Sep 3rd


2:35 to skip the first shameless cash grabs.

Aug 31st

Beau Cantayre

love the show, this episode was a big turd. Didn't laugh once.

Aug 31st
Reply (1)

Ethan Stringer

This might be the least entertaining 2 bears I've ever listened to.

Aug 30th
Reply (1)

Buck Fruckster

Only podcast I know with a laugh track in the back. Please put him in a soundproof room, guy laughs at everything, waters down the actual funny moments.

Aug 30th
Reply (1)
Download from Google Play
Download from App Store








Sleep Timer


End of Episode

5 Minutes

10 Minutes

15 Minutes

30 Minutes

45 Minutes

60 Minutes

120 Minutes

Ep. 96 | 2 Bears 1 Cave w/ Tom Segura & Roy Wood Jr.

Ep. 96 | 2 Bears 1 Cave w/ Tom Segura & Roy Wood Jr.