But here we are, two decades later, and the news that Martha and Snoop have just been hired by VH1 to host a cooking show together (titled Martha & Snoop’s Dinner Party) doesn't actually seem completely insane. Which is, in and of itself, kind of insane. Maybe the world might look at these two very different humans, making this probably-comedic show together, and take it as an example of how success levels the social and cultural playing field ... but there's also something about Martha & Snoop's Dinner Party that's a little depressing.
After her arrest, 2004 conviction for insider trading, and subsequent prison sentence, Stewart had to shift some major gears before she could make her return to the public eye a successful one. Given that most of the people who liked her brand pre-jail-time declared her career over as soon as she was convicted, Stewart did the smartest thing she could: Post-release, she started juxtaposing her squeaky clean WASP image of old with a very palpable edge.
Snoop is not the kind of guest Martha Stewart could invite onto her show before she'd done some time, but a 2008 clip in which Snoop goes rogue on Martha as she's showing him how to make the most fattening mashed potatoes in the world remains a YouTube favorite. By the time the two got back together in 2015, under the guise of making Christmas brownies, the double act was almost entirely centered around weed jokes.
Last year also saw Stewart resorting to joining in on Comedy Central's roast of Justin Bieber, even though her presence there made absolutely no sense whatsoever. "Look!" the joke seemed to be, "Martha Stewart says mean things too! What a crazy badass!"
Snoop has, of course, also adapted and changed over the last 20 years, but it feels altogether more organic. The biggest shift for the rapper came 10 years into his career, when he was finally permitted to show the world that he had an endearingly dorky, highly self-aware sense of humor. This came in the form of MTV's Doggy Fizzle Televizzle in 2002 -- the first time he realized that people liked it when he put himself next to non-"hood" things and carried on being Snoop. (The first episode of Televizzle put him in a bus full of senior citizens and gave him a microphone.)
Snoop's non-music profile peaked with the role of Huggy Bear in 2004's Starsky & Hutch remake -- a role that was probably supposed to be amusing because pre-fame Snoop literally worked as a pimp. (Hilarious, obviously.) Even with that in mind, he was still one of the best things in the movie.
Since then, Snoop's done everything from GPS voiceover work to a GGN radio show to inventing a new reggae-based persona for himself named Snoop Lion. One gets the impression that Snoop has a hard time saying no to anything; that if something looks like it might be fun for him to do, and that he might make some money out of it, that's an automatic yes. His brand is far from delicate.
Martha Stewart's reasoning for signing on to a cooking show co-hosted by Snoop Dogg looks considerably more contrived. Stewart's whole brand has been under siege for a few years now, thanks to new competition from high-end companies started by a new wave of rich-white-lady homemakers. It's clear she's feeling threatened: she's talked some sh*t about Goop's Gwyneth Paltrow several times, when she would be much better off trying to collaborate with her.
To make matters worse, Martha is having difficulty keeping up her down-with-the-kids image -- which is not surprising when that's not, naturally, who she's ever really been. Stewart's recent outburst about millennials, in which she labeled an entire generation lazy and stupid doesn't exactly endear her to a younger audience. It's really hard to like someone, even ironically, when they've just said about you: "They don’t know anything… They know how to make money and how to develop software, but they don’t know how to plant a tree."
In the end, Martha Stewart needs this TV show more than Snoop does, because she desperately needs people to like her more right now -- something Snoop's never really had a problem with. Stewart needs to show the world she still has something to offer, and if Snoop's by her side, she knows people will tune in for the odd couple act. Snoop's laid-back presence is just about the only thing on Earth that genuinely makes Martha Stewart seem not so uptight.
In the end, this might be a good show. It might be a funny show. But Snoop and Martha (and their writers) should keep in mind that it's hard to keep a single joke going for an entire season of anything, and make plans accordingly. Snoop has the ability to move onto the next thing and be just fine; he's the personification of going with the flow. Stewart's proven herself to be a survivor before, but she's scraping at the bottom of something for laughs here, and instinct says you don't bounce back quite so easily from failed self-parody.
Are we not giving her enough credit? Is Martha suddenly going to seem down-to-earth in a cool, street-smart, yet not desperate way? It'd be lovely to be surprised -- but either way, joke's on us: We'll just have to tune in this fall to find out.