The reason why Telltale Games exists, even if it wasn’t their first game to come out. The story goes that a team at LucasArts was handling follow-ups for Full Throttle and Sam & Max Hit the Road, but the projects got cancelled over concerns that there wasn’t a market for adventure games anymore. Key personnel still very much interested in making adventure games bailed on LucasArts and formed Telltale. The goal was always to make an episodic Sam & Max title, but Telltale worked their way up to it, first producing a small tech demo (Telltale Texas Hold ‘Em), then earn capital through a couple easy-to-obtain licenses (Jeff Smith’s Bone, CSI). With money in their pockets and Steve Purchell’s blessing, Telltale took their big swing and produced what is probably Sam & Max’s biggest, best-known incarnation.

…and before we go any further, let us stop to admire the significance of all this. Please, indulge me for a couple paragraphs.

Sam & Max are essentially underground comix characters, created by Steve Purchell…’s brother. When they were kids, Purchell’s kid brother Dave drew these comics of a rabbit and dog detective, and Steve drew over-the-top parodies of them to mess with his brother. Dave gave Steve the rights to these dorkuses as a birthday present one year, and Steve developed them into the verbose, satirical, gleefully insane Freelance Police we know and love today.

The characters debuted in a series of comics, which Purchell published as a side hustle to his day job. Eventually, that day job was to be an animator and illustrator for LucasArts (we have Purchell to thank for the fabulous coverart for titles like Maniac Mansion and Zak McKracken). LucasArts put out a quarterly periodical, to which Purchell started contributing Sam & Max comics… really because he could. The fine folks at LucasArts loved the Freelance Police so much that they started hiding them into games (this is jumping ahead a little bit, but my go-to example is Max inexplicably showing up as a friendly NPC in Jedi Knight). Eventually, someone at LucasArts realized they technically had full rights to the characters, so with Purchell on-board, the studio put out Sam & Max Hit the Road. Then there was the TV show, and more comics, and…

…well, not to put too fine a point on it - an entire game studio, one that has won countless awards for producing several of the most important games of its era, was founded with the express purpose of producing a new Sam & Max video game. Two studios, if we count the later Skunkape Games. All this from a kid messing with his little brother. You gotta love that.

With all this established, and knowing the house Sam & Max built out of Telltale, I’ve always found it striking how unconfident Telltale’s run of Sam & Max starts. It’s never bad, but it takes until “The Mole, the Mob, and the Meatball” - the third episode - before you really feel like Telltale gets what they want to do with these characters and this world. Before then, you have “Culture Shock”, which frankly feels so aimless and inconsequential within the scope of Season One that I can’t think of it as anything but a pilot episode. The main villain of the season doesn’t even show up! “Situation: Comedy” is a good high concept and feels like a better introduction to the characters, but it’s wanting for a big capstone or highlight moment to sell the whole thing (though I can’t hate Mr. Featherly, and there are lots of good throwaway lines during the ‘Cooking Without Looking’ segment).

But “The Mole, the Mob, and the Meatball” is where it starts to pick up. ‘Ted E. Bear’s Mafia-Free Playland and Casino’ is the joke that finally sold me on Sam & Max. And then ‘Just You And Me (And Ted E. Bear)’ really sold me on it. I think a decent amount of the first two episodes feel like they’re just extreme examples of adventure game silliness, and it isn’t until you hit that third episode and the change of scenery that you finally get, “oh, no, this just happens to be the heightened reality these characters exist in; adventure game silliness is part of the joke here”.

(as a quick aside - I’ll comment on changes made overall in the remake if I ever get around to playing that version, but I’m a little bummed that they changed the explanation for the ‘skinbodies’, since that was a favorite line as well. Definitely get why they made that change though)

The rest of the season is hit after hit. “Abe Lincoln Must Die!” has a ton of great dadaist political commentary and introduces one of the all-time greatest Sam & Max side characters in Agent Superball (plus, West Dakota). “Reality 2.0” is a fun send-up of internet and video game culture, with a decent amount of the jokes still holding up. “Bright Side of the Moon” is probably a step down from its predecessors, but there are still plenty of classic moments, like the complete lack of an explanation for how Sam & Max can drive to the moon, the payoff for Bosco’s Inconvenience, and the final confrontation.

I honestly think “Save the World” remains my favorite set of Sam & Max’s video game outings? “Hit the Road” is probably stronger overall, but I don’t think the series has given me anything as nakedly funny as a lot of this season’s highlights. Later Telltale seasons have their moments - “The Devil’s Playhouse” comes pretty close at times - but this is my easy pick for the one to play to get you into Sam & Max. Just… stick with it for a couple episodes.