| Boondocks! |
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I like Frazz, which has funny kids and a little taste of the philosophical side of Calvin and Hobbes. Frazz is particularly good if he's into running or biking, but not required to enjoy it
Could also get him a subscription to the Washington Post so he can read the comics daily and maybe look at a little news on the side. |
| Timmy Failure is the closest to Calvin and Hobbes I have found, complete with the possibly-imaginary sidekick, rivalry with a girl-next-door, advanced vocabulary, and the main character could very well be named "Calvin, only in middle school." |
| Mutts |
| Hyperbole and a Half is another classic |
We live Phoebe and Her Unicorn and Ozy & Millie, both by Dana Simpson. |
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Strange Planet, by Nathan Pyle
https://www.nathanwpyle.art/ |