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What happened after The Ride ended?
The 5th Dementia is an alternate dimension that Old Man - Schmitty’s father, according to one of the outtakes - introduced Schmitty to, without bringing it up to any of the other hosts who were trapped in the Bottom. Meanwhile, Troy Stevens, a Time Lord, flew his TARDIS (in the form of a TV game show set) to the Bottom to rescue Cookie and Nate.

In their travels, Schmitty and Old Man later met the Pirate whose gold was lost in the curse that began Volume 6; the pirate put a curse of his own on Schmitty, and once the player(s) had accumulated $1 million, Schmitty too would be freed. Old Man, Cookie and Schmitty were reunited back in this world for the 2011 and subsequent editions as announcer and host, respectively, while Nate would make his return as a Binjpipe content creator in Full Stream. Since Buzz and Guy haven’t popped up since The Ride, we can only assume they're still stuck at The Bottom.

The Ride was supposed to be the last YDKJ game, ever.
As evidenced by the end of floor 999 in the Ride, where Nate and the producer note they are completely out of questions, and share (not very friendly) goodbyes. One can only speculate as to why the series (thankfully) is still going strong, but one cannot help thinking that when The Ride was written, it was meant as a grand finale, especially with three of the potential endings in mind.

The "Games" floor also has a few questions that could possibly hint at this being the case, most notably a question where Nate criticizes [1] for being on its fourth edition - which was also the volume number for The Ride - and states that the well’s going to run dry eventually.

The You Don't Know Jack series unintentionally has a coherent metaplot
No, seriously.
  • YDKJ in-universe started as a TV game show hosted by Nate Shapiro. It became a smash hit, one of the hottest things on TV. Nate Shapiro became a household name as he began receiving bit roles in TV shows and movies, thanks to his newfound success. Unfortunately, like so many other overnight sensations, he got into the seedier side of showbiz, and, already feeling he was about to be canned for refusing to star in the spinoffs planned by the network, he left the show and eventually had a stint in rehab.
  • After several seasons and spinoffs, the YDKJ phenomenon ended up suffering from over-saturation and fell out of the public eye. While it still had an audience, it wasn’t as hot as it once was. Buzz Lippmann replacing Nate after the first season was the first blow, and while they quickly replaced him, the damage had been already done. Eventually, the network decided to put the show on hiatus and reinvent it, which led to The Ride.
  • You Don't Know Jack: The Ride was at that point the most ambitious game show ever imagined, from it's elaborate, industrial-inspired set, to different themed topics that the questions would focus on every episode, to using not one but FOUR hosts in rotation (including the much-hyped return of clean and sober Nate Shapiro). However, all this was extremely expensive, even when they taped several episodes a day over the span of a few weeks. Halfway through production, the network's new management pulled the plug on further tapings, leaving the crew to retape portions. The YDKJ production team would be vindicated when the network decides to air The Ride to recoup their losses, and it became the most popular season since the Nate Shapiro days; to this day, the show still has a cult following.
  • The success of The Ride’s reruns led to the production of 5th Dementia; however, lacking the cutting edge feel and cynicism of The Ride, it wasn't as successful and the show got cancelled until the network leadership was shaken up again a few years later.
  • This led to the infamous third reboot of the series, You Don't Know Jack: The Lost Gold. Between the cheesy low-budget set, gimmicky 'haunted show' premise, and Schmitty's asking price to do the show taking so much of the show's budget that they ended up firing every other staff member except for Old Man, The Lost Gold was an absolute disaster, and it seemed like YDKJ was finally dead.
  • ... Until YDKJ's copyright expired and Nate Shapiro would swoop in obtain the rights to it, wanting to bring new life to the franchise that launched his career. He'd produce a YDKJ webseries hosted by Cookie, featuring previous contestants going solo. (This would be the Webshow).
  • Shapiro's new YDKJ introduced new fans to the show where high culture and pop culture collide as well as getting old fans to stand up and take notice. Eventually YDKJ would be picked up by a new network, and has become a smash hit rivaling that of the original.

Binjpipe is going to show up again
This is more of an educated guess than a WMG, but At the end of the Escape the Simulation episode of YDKJ Full Stream, it was revealed that Binjpipe is actually trying to take over the world. Now, if this plot thread were to go anywhere, newer YDKJ games might have Binjpipe as the villain, possibly spreading to the rest of Jackbox Games. Here's where things get more WMG. During the post-game content of the last episode, Nate Shapiro states that anyone trapped in Binjpipe should be able to escape in three or four years, with a margin of error at about 7000. This could be a general release date given by the developers for the YDKJ where Cookie tries to escape, with the margin of error being the devs saying "Maybe, if things go well." It could even involve Trivia Murder Party, with it being the other trivia game that Jackbox Games makes, that would be in the story as the trivia show to stand up to YDKJ.

The Binjpipe Lady is the same person that was in charge of the elevator in The Ride
The Ride’s framing device involved an elevator that took the players down to themed floors every episode, with a rather cynical lady instructing the players and occasionally asking them random questions or changing their names as she saw fit. Unlike the previous waiting room hosts, who would willingly type in usernames for all three players, the elevator lady would not accept this behavior and shut down the game instantly. At the start of many an episode, the lady states that she’ll "see you at the Bottom", implying she inhabits the area, but when we finally arrive at the Bottom, she’s nowhere to be seen or heard, in stark contrast to the other hosts. This could mean that she was never trapped like the other hosts were.

Similarly to the elevator lady, the Binjpipe Lady is rather sardonic and cynical, but now that she’s in charge of her own streaming service, the power seems to have gone to her head. While during her stint as an elevator lady she would simply mess around with the players, the Binjpipe Lady instead directly interacts with Cookie while tending to ignore the players. By the time their secret is revealed, it’s clear that there’s no way they can be redeemed.

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