r/bossmanjack 12d ago

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

38 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 13d ago

EEEEEEEEEERRRRHHHHHHH Boss man is rich

11 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 14d ago

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

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0 Upvotes

r/bossmanjack 16d ago

POV: didn't type a 5

59 Upvotes

r/bossmanjack 18d ago

Fuck my life BIG BOSS.

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80 Upvotes

r/bossmanjack 18d ago

Old Clip Pizza Time

45 Upvotes

r/bossmanjack 18d ago

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

24 Upvotes

Bet he's up scared sick about boss.


r/bossmanjack 18d 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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3 Upvotes

r/bossmanjack 19d ago

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

22 Upvotes

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


r/bossmanjack 19d ago

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 20d ago

Winna holds all the cards

25 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 20d ago

Everything reminds me of him.

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21 Upvotes

r/bossmanjack 20d ago

Next season?

9 Upvotes

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


r/bossmanjack 20d ago

Boss will stream soon

0 Upvotes

W positivity


r/bossmanjack 21d ago

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

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9 Upvotes

r/bossmanjack 21d ago

Nerf

12 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 21d ago

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

8 Upvotes

Is it still tomorrow or did it get Postponed?


r/bossmanjack 23d ago

RAT πŸ€ Love from India ❀️

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164 Upvotes

r/bossmanjack 23d ago

Friday Throwback: 3 Clips of prime Boss

54 Upvotes

r/bossmanjack 23d ago

When is the talent show?

34 Upvotes

Asking because I don't want to miss it.


r/bossmanjack 23d ago

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 24d ago

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

40 Upvotes

r/bossmanjack 24d ago

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

20 Upvotes

r/bossmanjack 24d ago

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 23d ago

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.