RetroGaming

Ms. Pac-Man (Genesis) is fully co-op throughout, and has adjustable difficulty by choosing smaller maps.

Mega Bomberman (Megadrive) and Super Mega Bomberman (SNES) both have multiplayer mode where players can team up against bots, and the bots have adjustable difficulty (different bot skins have different AI).

Edit: Re violence - you blow each other and bot players up with bombs. Players that die disovle the way Pac-Man does.

Dashin' Desperados (Genesis/Mega Drive) is a racing platformer, where the adult can control the difficultly by slowing down or backtracking.

Edit: Cartoon violence - you can freeze each-other, light each-others shoes on fire, and stuff like that. And everyone recovers in cartoon timing, of course.

Super Baseball Simulator (SNES) is competitive, but can be really chill if the adult player throws easy pitches, and the super powers are hilarious.

"Toejam and Earl: Panic on Funkotron" (Genesis) has a very well designed "little kid mode" in the options, and it's still really fun.

Edit: Example regarding violence - you get to throw jars at humans to trap them for transport back to earth. And you need to watch out for bowling balls falling out of trees.

World of Illusion (Genesis)

from a sega childhood my top:

• toejam and earl
• micro machines
• world of illusion (mickey and donald)
• California games
• Bonanza Brothers (has guns but in game they are tranquilizers and enemies wake up)

Kirby Superstar (SNES) is great for this, I play it with my 5-year-old. The second player plays as the "helper" character, and when they die, Kirby can create them again. It effectively plays like a "buddy mode." That game is also one of my all-time favorites just for what it is, so I'm a bit biased.

Super Dodge Ball!

My Famiclone childhood:

Mario Bros (the first one, with POW block in the middle.) https://en.wikipedia.org/wiki/Mario_Bros.

Battle City, known more by its pirated version name: Tank 1990 https://en.wikipedia.org/wiki/Battle_City

Sonic 2. Make him be tails. As is tradition.

Wai Wai World 2 on Famicom emulator. Don't need to know any Japanese to play and it has great cartoony sprites.

Bubble Bobble (NES) is great two player, though you're competing

Buster Bros (PsOne, and probably others) probably one of my top 5 co-op games of all time

Micro Mages (retro despite being released in 2019 because it plays on original NES hardware) probably top co-op of all time for me

There's quite a bit more but have various degrees of violence so won't recommend those (Contra, Heavy Barrel, Silk Worm, Jackal, Life Force, etc)

Battle City

You know what? Gyromite and Stack-Up, the games made to be played with R.O.B. You play the robot. I don't know many co-op multiplayer games on the NES. Maybe Chip & Dale, or Mario Bros. (not Super, the arcade game - though in 2025, I suggest Kaetekitta(sp?) Mario Bros., the rerelease). Bomberman might have cartoon violence, but I don't think it's going to scar a kid.

On SNES, there's Secret of Mana if you want to try for depth. I forget if any of the sports games let you go co-op. Pocky & Rocky (and other cute 'em ups) might be fun too.

Actually, general suggestion, cute 'em ups. Cotton, Twinbee, Fantasy Zone, Air Zonk, and many of the Parodius incarnations (obviously Sexy Parodius notwithstanding).

Are you committed to using the R.Pi1? You could emulate on your computer or phone (connected to the TV) to have way more options.

How adept is your little one with games? My 4 year old loves any and all Mario games. He plays sitting on my lap. I celebrate his successes and he passes me the controller when he gets to a section too difficult for him. This is mostly with Mario 3D land (3DS) these days.

I would say that most retro games can be enjoyed by a 5-year-old (having once upon a time been a 5-year-old playing some of them myself), but the first one that comes to mind is Donkey Kong Country.

You both can play Goof Troop. It's a Co-op game with Goofy and Max as protagonists, it's very funny.

Mortal Kombat is pretty tame I hear.

( ͡° ͜ʖ ͡°)

Sonic the Hedgehog 2. Little one can be Tails and play coop.

A GREAT game to play with kids is called "Stacking". Looks like there's a Linux version so you might be able to get it running on the Pi:

https://en.m.wikipedia.org/wiki/Stacking_(video_game)

PlayStation 3, Xbox 360, Windows, OS X, Linux

The gag is this...

You play the smallest of a set of Russian nesting dolls and you want to re-unite with your family.

In order to do that you have to solve a bunch of puzzles in a world filled with other Russian nesting dolls.

You can jump into any doll one size larger than you, and you can jump out to be one size smaller.

Each doll has a specific skill or ability, so by swapping bodies, you use the various skills to solve the puzzles.

The challenge is, you might find one that has the right skill, but you're too small to jump into them, so you have to find the right chain of dolls to size up and size down to do what you need to do.

Trailer:

https://youtu.be/oEJtypcyL5I

Turtles in time

Super Mario by far IMO, basically all of the games.

5yo is probably still too young to understand Zelda.

TMNT Turtles in Time on SNES. Its a fun game and kids can button mash, and turtles are still relevant today. Puzzle games like tetris can be good for using the brain. There were a ton of puzzle games in the snes era, like bust a move (puzzle bobble), yoshi's cookie, puyo puyo (kirby's avalanche), and many more.

I would mostly avoid NES because it looks really dated, aside from a handful of the real classics like Super Mario Bros 1 & 3.

Nobody's gonna say hide and seek huh? 🤷

City Connection, Bugs Bunny's Crazy Castle. While neither are co-op my mom and took turns playing crazy castle on the nes when I was a kid and we beat it. Core memory right there.

I think Tetris or Doctor Mario had 2 player modes but I'm not sure.

Does Sonic Spinball on the Genesis have multiplayer?

My kid used to love one of the Kirby games for the Wii, where the three of us could play at the same time. I can't remember the name of it, but I'm pretty sure it was previously released for the SNES. It was the one with Armor Knight, if I'm remembering the character name correctly.

Hard to beat Super Mario Brothers. I tried other classics, bunch of arcade games, but my son never liked them. Ms. Pac-Man might work. The big hit with us was Wii sports.