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Humble Bundle usually has an annual bundle of all Jackbox games, and the collections go on sale on third party sites (Fanatical and Greenmangaming are cheap and trustworthy).
- the quintessential Quiplash (Cards against Humanity but you write your own answer)
- the brilliant Fakin It: Social deduction (who's the liar)
- the hilarious Tee KO (Note: Artistic skills needed!)
- Trivia Murder Party (Trivia with a twist!)
- Guesspionage - definitely the weakest but still fun (guess real world statistics)
I had such a blast playing Drawful (basically skribbl.io) from JPP1 but the pack itself is somewhat obsolete (newer packs have better game sequels) so I'd recommend picking up the standalone sequel Drawful 2.
If you enjoy playing these then I would recommend purchasing all the other packs and having a go at them!
Jackbox 5 is also a must because of Mad Verse City and Patently Stupid. The other stuff is kind kind of whatever.
Jackbox 1 is probably not worth your money as most of the game in it have gotten sequels, are available seperately, or just aren't really good games.
Jackbox 2 is kind of the same deal, though Jackbox 2 has Quiplash so that might be reason enough to get it. But Jackbox 3 is kind of a better choice if you want Quiplash and some better party games.
Jackbox 4 is an iffy choice. If you have friends who really like stuff like Monsters Dating Monster, then it's a good enough buy. The game also has Survive the Internet which can be almost as fun as Quiplash.
Jackbox 6 is the new title and it's really good too. Probably a good idea to get since it has Joke Boat, Dictionarium, Trivia Murder 2, and Push the Button (which is like Fakin It but capable of stream play)
Your choice of jackbox really depends on you and your friends. Some people dig games like Bracketeering, Guesspionage, Fibbage, and Don't Know Jack, but other people just like to have mindless fun with the likes of Quiplash, Survive the Internet, and Dictionarium, where the game encourages you to be as obscene, vulgar, and as wild as possible.
If you have the time, then go watch gameplay of some of the different packs and decide what's best for you, but if you want the safest bet, get Jackbox 3.
To put it simply,
Jackbox 3 is a must.
Jackbox 5 and 6 are good choices.
Jackbox 4 is an iffy pick.
Jackbox 1 and 2 can probably be skipped.