Bossmanjack is Back and WINS 45k

(25:3)

BossmanJack Needs Help

(7:18)

bossmanjack wants to buy a bmw and take care of his family,i love dice,joytongue,what that 6k there?

(25:44)

BOSSMANJACK BACK ON PLANES PT 2

(29:29)

BOSSMANJACK BACK ON PLANES

(26:38)

BossmanJack actually WINS 185k

(28:16)

BossmanJack Informs Drug Dealer He Lost It All \u0026 Slam Dunks Phone

(5:53)

bossmanjack wants to show us how to lose 3k in 20sec, new whale is a rat,rat dad, flirts with dealer

(32:11)

GOOBR $15,000 LIMBO

(9:18)

Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary

(12:26)

The Most Degenerate Gambling Streamer | BossmanJack

(18:21)

bossmanjack wants to destroy his pc after fumbling x2 10k, MOM! DAD!, \

(50:46)

BossManJack Losing His Father's Money

(13:27)

نصر الدين | ســ ــفاح المعمورة . منظور مختلف

(17:13)

Degenerate Gambler Losing all His Money.

(1:47)

The M4 motor can't be SAVED

(18:57)

I Don't OWN my Lamborghini

(19:50)

Bossmanjack discord stream, Dallas BINNED! Microwaved ice cream and skating !

(25:19)

The Saddest Man Alive (Ft. Drake/Andrew Schulz/DJ Akademiks)

(10:10)

Onlyusemeblade’s Girlfriend Realises She’s Failed In Life While Blade Is Passed Out Behind Her

(44)

XQC GOES ALL OUT ON PLINKO WITH $3.5 MILLION 🤯

(1:3)

SeasideMark - QUTTING YT!! And, He Really, Really, Really means it this time guys - cue WHITERUN!!!!

(2:56)

The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary

(25:7)

BossmanJack Is Addicted To Losing

(14:41)

bossmanjack wants to f a dude compilation

(5:55)

BossManJack Back To Begging For Juices Doesn't Have A Dollar To His Name

(28:34)

BOSSMANJACK PLANES LOSES

(22:33)

BossmanJack says he can lead MEN

(16)

BossmanJack RAGE QUITS and BREAKS EVERYTHING (WE'RE SO BACK)

(2:8)

bossmanjack wants to run a poll to see who is acting like the better person, good luck to your chat

(25:2)