Elevate your streetwear game with the ultimate irony piece: the Pim and Charlie Shirt. Featuring Pim and Charlie like you’ve never seen them before—iced out, suited up, and flashing serious cash—this tee channels the viral ‘hard image’ aesthetic that’s dominating TikTok and meme culture in late 2025.
Smiling Friends Gangster Shirt – The Gangster Pim & Charlie Money
Step into the world of ironic fashion with the shirt, a bold and hilarious piece of apparel that flips the script on the show’s wholesome premise. This shirt features an exclusive, high-definition graphic of Pim Pimling and Charlie Dompler trading their usual Smiling Friends uniforms for exaggerated “hustler” attire.
Charlie is decked out in a sharp green pinstripe suit and fedora, flashing gold grillz and a stack of cash, while Pim embraces the street look with a bandana, sagging jeans, and an oversized bling pendant. It is the ultimate collision of Smiling Friends awkwardness and early 2000s “gangsta cartoon” aesthetic.

Why Did This Design Go Viral?
This design went viral because it taps into the “Gangster Cartoon” nostalgia trend and the “Hard Image” meme format. In the early 2000s, it was common to see unauthorized shirts of characters like SpongeBob or Popeye dressed as mobsters. Internet culture revived this in 2024-2025 as a form of “ironic drip.” Seeing Pim—a character defined by his pathetic optimism—dressed as a hardened street thug creates a visual oxymoron that resonates perfectly with the surreal, unexpected humor of Smiling Friends creators Zach Hadel and Michael Cusack.
Product Specifications:
- Classic T‑Shirt (G500): 5.3 oz, 100% cotton for everyday comfort; Ash is 99% cotton and 1% polyester, Sport Grey 90% cotton and 10% polyester.
- Ladies T‑Shirt: 100% preshrunk cotton; Ash Grey is 99% cotton and 1% polyester, with a feminine scoop neck and slightly tapered fit.
- Crewneck Sweatshirt (G180): 8 oz fleece made from a soft 50% cotton and 50% polyester blend for warmth and durability.
- Pullover Hoodie (G185): 5.3-ounce, 100% cotton (99/1 cotton/poly (Ash) & 90/10 cotton/poly (Sport Grey)
- Long Sleeve T‑Shirt: 5.3 oz, 100% cotton; Ash is 99% cotton and 1% polyester, Sport Grey 90% cotton and 10% polyester for added softness.
- Youth T‑Shirt: 5.3 oz, 100% preshrunk cotton; Ash is 99% cotton and 1% polyester, Sport Grey 90% cotton and 10% polyester for easy everyday wear.
- Men’s Tank Top: 5.3 oz, 100% cotton with taped neck and shoulders and a tearaway label for extra comfort.
- Women’s Tank Top: 4 oz fabric, 60% combed ring‑spun cotton and 40% polyester jersey, laundered to reduce shrinkage and designed with a flattering fit.












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