05:44
Bossmanjack clips to help the content drought, JOIN DISCORD LINK IN DESCRIPTION
09:47
Bossmanjack has a new sponsor, most boring one yet
08:14
Bossmanjack's Experience with Rainbet...
05:55
Bossmanjack FREAKS OUT After Losing all of his Money
08:03
Bossmanjack Mod gets Verbally Assaulted and Binned (Full Chat Logs)
06:43
Bossmanjack wins $1400 on new site, But will he lose it all?
07:28
Bossmanjack on Super Shady Sites now that he has no Sponsor
02:48
Bossmanjack Clips for While he has no Sponsor
03:28
Bossmanjack FIRED AGAIN From his Sponsor, Is Tired of Being Bullied
12:34
Bossmanjack Can't Stop Losing FAKE MONEY
06:40
Bossmanjack Reminisces on the Good Old Days, Isn't Having Fun Anymore
08:30
Bossmanjack Enters the Minefield... Threatens to Quit Streaming Again
12:25
Bossmanjack DESTROYS His Keyboard After Losing it All
05:21
Bossmanjack Can't Help Himself, Keeps Losing it all on Originals
05:52
(FINALE) Bossmanjack's Blackjack Chronicles Part 3
08:18
Bossmanjack's Blackjack Chronicles Part 2
12:34
Bossmanjack's Blackjack Chronicles Part 1
08:27
Bossmanjack ACCIDENTALLY TIPS $15k, Loses $35k on Blackjack
08:14
Bossmanjack DESTROYS his Mouse After Losing $80k
16:11
Bossmanjack Loses $40k on a Private Discord Livestream
03:52
Bossmanjack Feeling Very Sick, Destroys Mouse After Losing it all
06:57
Bossmanjack Gets hit by Karma HARD, Loses $3k
05:43
Bossmanjack Back to Losing it all After Getting out of Jail
11:34
Bossmanjack Celebrates Getting out of Jail by Losing $15k
05:38
Bossmanjack OUT OF JAIL, but will he lose it all again?
02:31
Congratulations, Bossmanjack! (2024)
01:34:08
Full Bossmanjack Convos With Former top Mod (From KiwiFarms)
05:13
Bossmanjack FIRED From Shuffle, Loses $10k to Celebrate
09:21
Bossmanjack Feeling Good After Winning $5k, Loses it all Immediately
06:38
Bossmanjack Can't Help Himself, Loses Money he Needed for Dealer
07:11
Bossmanjack SMASHES Keyboard After Losing $500
14:32
Bossmanjack Keno Makes a Return Goes Shopping for Gold Coin
03:45
Bossmanjack Speedruns Losing his Paycheck
18:51
Bossmanjack Numb to the Losing Can't Seem to win Anywhere
09:21
Bossmanjack: The Dice King Won't Stop Losing it All
09:04
Bossmanjack Broke and Back to Losing his Viewers Money
11:01
Bossmanjack Doesn't Have a Dollar to his Name - Sponsor Won't let him win
07:03
Bossmanjack Scrapes Bottom of the Barrel, Threatens to Leave Sponsor
05:53
Bossmanjack Officially BANKRUPT! Lost the Entire $180k
06:29
Bossman CONTINUES to Lose the Rest of the $180k