To be fair, the character playing with the jukebox apparently had Downs syndrome. So he's allowed to be cringy.
Ruth is actually the main one which it's centered around; Tucker apparently learned all he knows about Biggie from her.
Let's pretend for a second that folks with Downs are cringy - you don't think a more palpable, relative, and appropriate artist that was in line with the show's surroundings (White trash, Middle America sequestered town) would have more of an impact? Using Biggie as a juxtapose in a white-crime drama is something I'd expect from a show 20 years ago, not in 2018 - it's not even something that one could buy as being a motif for escapism for Ruth. Not only is it tacky, but it's lazy, and to make matters worse, it was used as a constant. I don't know what the hell the writers were aiming to achieve with that, but then you could apply the very same to everything else in the show.