Q&A with Bob Mackey, Author of Day of the Tentacle March 01 2023

Bob Mackey is the author of a new book about the PC classic Day of the Tentacle, currently funding on Kickstarter. I caught up with Bob over email to discuss adventure games, animation, comedy, and puzzle design. - Gabe Durham
Could you tell us about how you first discovered Day of the Tentacle? Were you already playing a lot of adventure games at the time?
After playing and falling in love with the Maniac Mansion NES port, I became an adventure game fan with no real access to a PC: the sole platform where the genre thrived. So when Day of the Tentacle appeared at my local game store in 1993 (in its eye-catching five-sided box), I absolutely coveted it—and should have bought it anyway, seeing as it's now an incredibly rare collector's item I don't have the guts to drop several hundred bucks on three decades later. We didn't get a family PC until 1996, and as soon as it entered our home I found myself catching up with 15 years of adventure games. Of course, Day of the Tentacle was one of the first ones I jumped into.
In the book, you hit on the growing pains that the point-and-click adventure genre went through before  Day of the Tentacle came out. How did the DotT team benefit from the lessons of the past?
Day of the Tentacle was the first project led by directors Tim Schafer and Dave Grossman, two guys who had previously worked directly under Ron Gilbert on the first two Monkey Island games. This duo of releases essentially codified the rules all (good) adventure games adhere to, and Schafer and Grossman took these lessons learned and applied them to everything within Day of the Tentacle. The result is an experience that feels more refined than everything in the genre that came before it, and one that remains incredibly playable today.
Making a legit funny video game is famously very hard. Why do you think Dave Grossman and Tim Shafer succeeded where so many have failed?
Grossman and Schafer realized the limitations of technology at the time, which is why so much of the DotT's humor isn't reliant on dialogue—in fact, voice acting entered the equation much later during the production. Of course, the dialogue is funny, and they nabbed some great actors to fill the roles, but the awkward pauses between spoken lines in games of this era couldn't necessarily sell jokes as intended. So DotT makes the right choice to rely on its visuals to communicate humor to an extreme other adventure games of the early '90s weren't attempting.
A lot of your work in recent years has been podcasting about The Simpsons and other animated shows, and Day of the Tentacle is often praised for its distinct animation style. Could you tell a little about the DotT team's approach? And how do you think they were able to pull it off with so much less space and frames than their TV & film counterparts?
Day of the Tentacle came about at a time when very few games had any formal sense of art direction. (Hey, 1993 was 30 years ago.) Earlier games featured cartoony visuals, of course, but DotT had an actual mission statement: "Let's make this look and move like a Chuck Jones cartoon." The artists behind the game closely studied classic animated shorts of the era, resulting in the most Chuck-Jones-like production possible at a resolution of 320 by 200. And they were able to make it work on just a handful of floppy discs using the same techniques of classic animation: strong poses and silhouettes that communicate everything you need to know about a character. (Not to mention stylized backgrounds that rely more on file-size-friendly abstraction than photorealism.) 
The puzzles in DotT are so goofy and clever. Do you have a favorite? And do you have one that you still have to look up online?
I don't want to completely give away all the steps, but there's a certain puzzle where you have to transform a cat into a skunk via a method that would feel right at home in a Pepe Le Pew cartoon. This isn't my favorite puzzle in terms of design, but it's the most evocative of how Day of the Tentacle is aspiring to be an interactive classic cartoon. And it felt absolutely natural to me as a kid who grew up watching close to 10 hours of Warner Bros. shorts a week on at least four different channels.
After growing up a Day of the Tentacle fan and working on this book project for years, there's absolutely no puzzle for the game I haven't memorized. If you see me on the street, feel free to ask for a hint!
There's been a resurgence of adventure games in recent years, including new games and remasters of old games. Have you kept up with the genre? Any games you'd recommend?
Return to Monkey Island released during the production of this book, and I can't recommend it enough; it stands alongside Day of the Tentacle when it comes to stellar adventure game design. And I also suggest that people don't sleep on the recent remasters of the Sam & Max episodic Telltale games. They've been lovingly remastered by some of the folks who worked on them back in the late '00s, and each episode is just so digestible, fun, and non-frustrating. Does everything I've mentioned so far have DotT co-director Dave Grossman in common? Perhaps.