10 Wanna Be Gangsters Jokes

Observational Jokes

Updated on: Jan 21 2025

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I saw a guy with a neck tattoo that said "thug life" but he was in line at a frozen yogurt shop. I didn't realize being a thug came with a side of sprinkles and a choice of toppings.
I saw a group of these guys trying to breakdance in the park. It was like a scene from a bad '80s movie, complete with cardboard on the ground and questionable dance moves. I think they confused gangster with breakdancer. Easy mistake, right?
Wanna-be gangsters are always bragging about their street cred, but the only thing they've ever hustled is probably a board game. "Yeah, I'm the Monopoly kingpin of my neighborhood." Sure, buddy, I'm terrified.
You ever notice how there are always these wanna-be gangsters walking around like they're auditioning for a low-budget gangster movie? I saw a guy the other day trying to pull off the whole tough guy look, but he ended up looking more like a confused penguin. Dude, it's the streets, not the South Pole!
Have you ever noticed that these tough guys always have the tiniest, yappiest dogs? I saw a guy with a Chihuahua the other day, and I thought, "Dude, if your dog is smaller than your ego, maybe you need to reevaluate your life choices.
I was at the grocery store, and I saw a wanna-be gangster in the produce section, trying to act all tough while picking out avocados. Seriously? Are you going to threaten someone with guacamole? "Give me your wallet, or I'll make you some delicious toast toppings!
Wanna-be gangsters love to throw around hand gestures like they're in some secret society. Dude, you're not casting spells; you're ordering a pizza. Keep those fingers in check before you accidentally summon the delivery guy.
You know you're dealing with a wanna-be gangster when they insist on wearing sunglasses indoors. I guess they're trying to protect their eyes from the dangerous glare of fluorescent lights. Watch out, we got a real tough guy over here!
These wanna-be gangsters are like human chameleons. One day, they're rocking baggy pants and oversized jerseys, and the next day, they've transformed into businessmen in suits. It's like they have a fashion identity crisis. Are they trying to join the mafia or the corporate world? I can't keep up!
I overheard a wanna-be gangster talking on the phone about his "connections." Bro, the only connection you have is the Wi-Fi at Starbucks. I doubt the real mobsters are discussing their business plans on speakerphone at a coffee shop.

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