Where do all the aging rappers go? When trends have rolled over to teenagers in tight pants with eclectic flows, when a rapper is more likely to sing than actually rap, when emotionally vulnerable lyrics are de rigueur, what’s a gangsta rapper to do?

These are the questions I imagine Snoop Dogg grapples with, as the “Uncle” to everyone in hip-hop slowly ages into Grandpa territory. There are, in fact, ways for an old rapper to age gracefully — you can get into the acting biz (I see you LL), you can go behind the scenes into the business aspect (here’s looking at you Jay), you can start producing movie and TV shows (hello Ice Cube), you can even brand yourself onto some electronics (good going Dr. Dre).

All these paths are credible and profitable means for a rapper to continue to earn a living after going platinum is no longer an option.

Click here to view a Grio slideshow of rappers over 40 who are keepin’ it relevant

However Snoop Dogg seems to eschew convention and his entire career longevity and retirement plan consists on a single ethos: don’t say no. Record a studio album on a floundering record label? Sure, don’t say no. Star in a bad movie? Sure, don’t say no. Record a song with Charlie Sheen? Sure, don’t say no.

I get it, the older you get, the less you care. You can take more risks, you care less about your image and what other people think about you. However there are limits to this carefree approach to life, and Snoop Dogg is definitely pushing the boundaries.

At the peak of his popularity, Snoop Dogg was a pioneer in his field. His ultra-smooth delivery, distinct style of dress, and amiable personality made him America’s favorite gangsta. However as time as progressed, Snoop has either a) given less thought to the long-term ramifications of his career choices, or b) content in making a joke of himself for money-making purposes. Because the things he’s doing now definitely don’t appeal to his core fan base.

Exhibit A: His last three albums have flopped. Everyone is allowed a sucky album or two, but three-in-a-row suggests a streak to nowhere. Though there were some strong singles from the albums (“Sensual Seduction” from 2007’s Ego Trippin’ peaked at #7 on the Billboard Hot 100), it’s hard to get decent promotion when you’re on a crappy record label.

Exhibit B: He acts badly in really bad movies. Soul Plane is an easy target, and perhaps his Huggy Bear in the Starsky and Hutch remake was appropriate, but his most recent character, Big Pu**y (with limited release this weekend) is getting reviews so bad, it’d probably serve him best to take his name off the credits. Says a movie critic at The New York Observer – “I cannot think of a movie more incomprehensible, moronic, pointless or abominable than a load of trash called The Big Bang.”

Exhibit C: He will rap on anyone’s track. Lately, it seems the only tracks Snoop is interested in recording are catered to white audiences. I.E.: Katy Perry’s “California Girls,” a song for an Australian singer named Jessica Mauboy, Prince William’s bachelor party song (what?), and the living catastrophe that is Charlie Sheen. Going mainstream is every artists’ dream, but there must be some sort of line drawn.

And that’s the problem. Maybe Snoop’s having fun experimenting and collecting checks, but he’s starting to lose artistic integrity. He’s becoming a parody of himself. This is a man who was once respected and admired, and now he’s rapping for Charlie Sheen? Really? Collaborating with Charlie Sheen is lower than low, a desperate publicity-seeking move you’d more expect out of Flavor Flav than a platinum-selling artist. The guy who was once the definition of cool has been diminished to working with TMZ stars. You can do better than that Snoop. It’s not all over for you.

This former gangsta seems to have been sterilized down to a non-threatening has been, an entertaining caricature of himself for white audiences. I have faith in Snoop’s staying power (who else can both acknowledge they’re a Crip and appear on a daytime soap opera?), but I’m starting to question who’s he’s staying for, and how far he’s willing to go.