Despite his other more extravagant tattoos, this relatively simple tat of Chris' home state of Connecticut is actually the one that caused him the most hesitation before going through with it — mainly because of its easily viewable location and size. Chris cites this tattoo as the moment he realized there was no going back from all of the tattoos he had gotten.
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Of all his tattoos, Webby’s Mario sleeve is his most famous — watch him give a tour of them on RapGenius here. It all started off with the Mario tattoo, which Chris got done on a whim after a night of heavy drinking in College Station, TX. This was followed by Boo the Ghost which he got done on his inner arm by Josh Glasser in his hometown of Connecticut. Then came Bowser on his bicep (Bowser also got repped in a song off of his Bars on Me mixtape). After slowly accumulating his first few tattoos, Chris decided to finish the Mario sleeve and got tattoos of Luigi, Toad, a “?” box, and a Piranha Plant coming out of a tube.
After running out of room on his left arm, Chris began going down his back, getting tattoos of a Bob-omb, Super Star, Cheep Cheep, Yoshi, and Chain Chomp, which all culminated in “a giant, badass Donkey Kong that sits right above my hip”. He has gotten criticism from his peers and elders that tell him he is going to regret getting cartoons tattooed all over his body one day, to which he responds:
Because hip-hop was built upon rags-to-riches stories where former dope boys like Jay Z became their own CEO’s, most aspiring rappers grow up thinking that all they have to do to achieve the “American Dream” is sell a few records and make their money. The reality is that even though more and more rappers are making millions off of rap, it is just as hard to ever to achieve true freedom through hip-hop. Label executives are always going to try to keep their artists subordinate, and the long-standing perception that no amount of money can validate hip-hop as an actual art form continues to hold them back. As Kanye put it: