So I'm not sure why nobody mentioned this, but there's another method to this achievement that's much much faster. In the settings on the main menu there's an option called Manual Censorship (or something similar) that prevents players from being able to submit drawings. So there's 2 options in this method (the second I list is faster).
Start the game with 3 players
On Player 1, censor players 2 and 3 then choose "everybody's in" to start the game
Draw a picture and submit with Player 1
Either click "skip this is offensive" or wait for the timer (make sure extended timers is off if you wait as it's 30 seconds instead of 60)
Repeat for the second round
Same players
The second and fastest way is to start with 7-8 players
On Player 1, censor players 2-7/8 then choose "everybody's in" to start the game
Draw a picture and submit with Player 1
Either click "skip this is offensive" or wait for the timer (make sure extended timers is off if you wait as it's 30 seconds instead of 60)
Same players
Just do 50 games and you're golden. I personally used Google Chrome. One normal tab, one Incognito tab, and 5 with SessionBox.
In either option, you can either minimize or even close out of the other player's tabs since you're only using Player 1 (and hopefully just skipping the voting to save time).
For me I was able to get this one done in about 30 minutes while actively skipping. I just used split screen on Windows and had Jackbox open on the left while I watched a show on the right. I found this in the comments of a Steam guide so I'll link it below. SimulationWithDaniel suggested it and sylvrain gave a more thorough explanation if you're looking.
https://steamcommunity.com/sharedfiles/filedetails/?id=21814...