Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary
12:26
Inside the World of BossmanJack - Rolling The Dice: Part 1 | A LolCow Documentary
50.4K viewsApr 10, 2024
YouTubeThe Redman
The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary
25:07
The End of BossmanJack - Rolling The Dice: Part 2 | A LolCow Documentary
101.5K viewsJul 5, 2024
YouTubeThe Redman
The Decay of Bossmanjack | A Lolcow Documentary
25:59
The Decay of Bossmanjack | A Lolcow Documentary
23.6K viewsOct 10, 2024
YouTubeRKH Media
The Terrifying Life Of A Professional Gambling Addict
12:09
The Terrifying Life Of A Professional Gambling Addict
9.1K views5 months ago
YouTubeODAAT Gambling Awareness
The Dark Truth Behind Gambling Streamers
27:37
The Dark Truth Behind Gambling Streamers
7K views2 months ago
YouTubeODAAT Gambling Awareness
BossManJack Rewind The 100k Loss
27:17
BossManJack Rewind The 100k Loss
73.6K viewsJan 9, 2025
YouTubeBossManLacks
Bossman Jack Rages After Gambling Everything (Addiction)
1:00
Bossman Jack Rages After Gambling Everything (Addiction)
2.1K views8 months ago
YouTubeODAAT Gambling Awareness
30:53
Bossmanjack Lost The Money Meant For His Dealer Begs For More
18.1K viewsJun 12, 2024
YouTubeBossManLacks
8:51
Bossmanjack Loses $6k During Rollercoaster of a Stream
7K views8 months ago
YouTubeCeeJ
22:31
BossManJack - Kicks Biggest Gambling Degenerate
149.3K viewsMar 25, 2024
YouTubeBillsYT
5:32
BossmanJack Losses and RAGES BIG
811 views8 months ago
YouTubeALT F4
10:40
BossmanJack Gets Donated $3000 And Loses It On Dice
40.5K viewsJan 22, 2024
YouTubeColonel Rat
1:50
Bossmanjack Loses $3,500 in One Minute "RAGE BETTING"
167.3K viewsSep 7, 2024
YouTubeBossmanJack Rage
14:33
Bossmanjack Loses $100K+ In a Week
96 views2 months ago
YouTubeMore CeeJ
2:02:07
BossManJack Up 15K Hits Big, Puts Some In The Vault will it stay?
39.2K viewsJan 12, 2024
YouTubeBossManLacks
33:23
BossManJack BIGGEST WIN From 170k to 50k Will He Still Get The Range Rover?
40.2K viewsJun 19, 2024
YouTubeBossManLacks
14:23
Bossmanjack wins the most money he ever has. Also, Bossmanjack loses the most money he ever has.
129.9K viewsMay 9, 2024
YouTubeBossManCrack
4:02
BossmanJack Got ARRESTED For BEATING HIS FAMILY!
1.1K viewsJul 4, 2024
YouTubeGrifterverse
Twitch
May 2, 2025
Twitchtwitchbossmanjack
59:10
BossmanJack WILD Gambling Session #bossmanjack
2.3K views4 months ago
YouTubeInturnet Dorcs
1:03:51
PickleTime LIVE Vod #55: Bossmanjack gets RINSED
95 views4 months ago
YouTubePickleTime LIVE 🔴
27:50
BossManJack Has Officially Lost All Of The 170K Rages Hard
84.6K viewsJun 21, 2024
YouTubeBossManLacks
4:00
Bossmanjack - ALL MEGA RAGES (June - July 2024 Version)
145K viewsJul 28, 2024
YouTubeBossmanJack Rage
7:51
BossManJacks Biggest Losses Part One
31.1K viewsMar 6, 2024
YouTubeBossManLacks
28:36
BossmanJack Loses Over $15,000 During a Stream, Rat Dad Ruins His Fun
60.9K viewsFeb 15, 2024
YouTubeColonel Rat
12:42
The Best Of BossManJack
32K viewsApr 4, 2024
YouTubeBossManLacks
1:04
Bossman Jack hits huge 500x win on Keno
5.4K viewsMar 9, 2024
YouTubeThe-Grind-Lifers
0:43
Bossman Jack Shows The Sad Reality Of Gambling
5.6K views8 months ago
YouTubeODAAT Gambling Awareness
25:00
BossManJack Permanently Banned From Kick
2.1K viewsJun 16, 2024
YouTubeBossManLacks
See more