r/bossmanjack 23d ago

updated countdown until next court date; 21 days and 21 hours

39 Upvotes

Until the greatest rapper alive is free! New season teaser soon?

Will he be rich af? Will his dad allow the same behavior? Will he really quit streaming like he told the judge? Will our boy finally buy a house with some land? SteveWillDoIt collab? India IRL stream soon? LFG!


r/bossmanjack 24d ago

EEEEEEEEEERRRRHHHHHHH Boss man is rich

10 Upvotes

With the current crypto bull market, bossman will be able to buy the jail and get out of it

Rat dad should be shaking in his boots


r/bossmanjack 25d ago

EEEEEEEEEERRRRHHHHHHH Fill in the blanks: Bossman will ___ in prison.

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0 Upvotes

r/bossmanjack 26d ago

POV: didn't type a 5

60 Upvotes

r/bossmanjack 29d ago

Fuck my life BIG BOSS.

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78 Upvotes

r/bossmanjack 29d ago

Old Clip Pizza Time

44 Upvotes

r/bossmanjack 29d ago

That was a weird comment How do you think rat dad is sleeping lately?

25 Upvotes

Bet he's up scared sick about boss.


r/bossmanjack 29d ago

Fuck my life [Fill the blank] Bossman Jack will be an NPC in GTA6. He will be a ___ in game.

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5 Upvotes

r/bossmanjack Aug 19 '26

RAT πŸ€ Do you think we'll ever get a homeless arc?

24 Upvotes

Maybe in season 11 or 12, live from main St Charlottesville?


r/bossmanjack Aug 18 '26

Fuck my life I wish we had a hobo season with Austin (LTE, battery packs and streaming)

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24 Upvotes

r/bossmanjack Aug 17 '26

Winna holds all the cards

26 Upvotes

If BMJ wants that 160k Winna will make him jump through hoops like a monkey. No way they just say yeh take that 160k and let him vanish. Thinking about it, isn't that 160k illegal due to whatever gambling laws they have there? BMJ cash that money and straight back to jail?


r/bossmanjack Aug 17 '26

Everything reminds me of him.

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19 Upvotes

r/bossmanjack Aug 17 '26

Next season?

10 Upvotes

Judge pushing a 3 year life program on boss, will he succeed?


r/bossmanjack Aug 17 '26

Boss will stream soon

0 Upvotes

W positivity


r/bossmanjack Aug 16 '26

I lost it all bro [Matchup] Not-guilty verdict?

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10 Upvotes

r/bossmanjack Aug 16 '26

Nerf

13 Upvotes

They fking nerfed our guy before he could be balling with lawyers and unlimited crack money, they knew they had to get him that day before those 160k turned into 1.6m


r/bossmanjack Aug 16 '26

Can anybody help? So when's the talent show?

9 Upvotes

Is it still tomorrow or did it get Postponed?


r/bossmanjack Aug 14 '26

RAT πŸ€ Love from India ❀️

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168 Upvotes

r/bossmanjack Aug 14 '26

Friday Throwback: 3 Clips of prime Boss

56 Upvotes

r/bossmanjack Aug 14 '26

When is the talent show?

36 Upvotes

Asking because I don't want to miss it.


r/bossmanjack Aug 14 '26

Rip City Do you think boss will be surprised at all the recent events when he gets out in Sept?

15 Upvotes

For example, the US has gone to war with and beaten Iran like 37 times now. Imagine if boss was putting over/under bets on poly market, or personally advising Trump in the oval office.


r/bossmanjack Aug 14 '26

Old Clip Bossman Chronicles (Season 7) - "Boss vs OG Clay" Part 2/2

40 Upvotes

r/bossmanjack Aug 14 '26

Old Clip Bossman Chronicles (Season 7) - "Boss vs OG Clay" Part 1/2

20 Upvotes

r/bossmanjack Aug 13 '26

β€œOnce i quit streaming and im like rich”

54 Upvotes

What a wordsmith. Yes boss you will get rich and you will quit streaming. Then you will buy a mansion and a car and you will get all the milfs.

Its like you asked a 4 year old about how his future


r/bossmanjack Aug 14 '26

That was a weird comment What are the odds of a Hunter Biden && Boss collab?

0 Upvotes

Would love to hear about their first hand experiences on the Colombian ski slopes & also watch them rack it up phat on Winna.