Boss Man Jack

40:24

The Crackhead Criminal Gambling His Life Away
Turkey Tom
1.8M views
14:23

Bossmanjack wins the most money he ever has. Also, Bossmanjack loses the most money he ever has.
BossManCrack
59K views
4:48

Bossman jack makes 22 grand from 500 then LOSES IT ALL
Trygve manshit
353 views
11:51

BossmanJack Wins $23,000. Loses it in 2 Minutes...
Colonel Rat
66K views
5:59

Bossmanjack First losing Stream after jail -20.000$ - Crying and sad
BossmanJack Rage
20K views
16:51

Kicks worst gambling addict gets worse - Bossman jack
Kiwi tapes
168K views
1:04

Bossman Jack wins 19k then loses it in 2 minutes!
Jonny Hicks
50K views
13:41

Bossman Jack is out of Jail
Biff the Wolfman
15K views
18:21

The Most Degenerate Gambling Streamer | BossmanJack
Nick Nobody
537K views
16:43

LUH TYLER Interview: Mr. Skii, Bossman D Low Collab, & Florida Lifestyle-Thenterview: Feat. Lainey B
THENTERVIEW Podcast
84 views
3:41

BOSSMANJACK PERMA BANNED ON TWITCH
OGClay
3.6K views
30:59

BossmanJack Wins Over $180,000 In a Single Day, New Record!
Colonel Rat
33K views
25:07

The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary
The Redman
22K views
12:26

Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary
The Redman
24K views
1:36

bossmanjack's greatest freakout ever
ContentGoblin
45K views
41:57

How bossmanjack lost 200k - Part 4 Finale
PickleTime
19K views
1:02

BossmanJack Loses $10,000 in 12.2 Seconds On Limbo
Colonel Rat
98K views
42:23

bossmanjack finds god in jail, 50k juicer is fake(doesnt realize it yet),jail story,6k shuffle bonus
IoIshtar - journeyman rigger
6.6K views
10:22

BossmanJack RAGE QUITS After Losing $9,000 & Awake For 3 Days
Colonel Rat
63K views
10:15

BossmanJack Has a Mental Breakdown, Blows up Multiple Keyboards
Colonel Rat
18K views
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