Things start off with Dr. Quintus Ratcliff taking Diana Love (the "riffing" is clearer than the dialogue, or at least more persistent in pointing out, that she's a sex trade worker) to his old mentor Dr. Ulbrect Olinger; Quintus is intent on proving to Olinger that past life regression is possible, and disparages Diana's intellect while she's right there. He then hypnotises her ("When you wake up I'll be the foxiest guy you've ever seen!") until she regresses to her past life Helene, locked up in "the Tower of Death" and about to be executed on suspicions of being a witch. Then, things start getting complicated, as Helene hears a voice from the future giving her advice on how to knock out the lone guard and get away. ("So she's a spirit guide slash self defence coach.") She flees through a rather cramped kingdom with a handful of people in it, each more bizarre than the next, ranging from the singing Digger Smolkin to the putty-enhanced crone Meg Maud to the somewhat dimwitted knight errant Pendragon to the shape-shifting genuine witch Livia and her rather less attractive imp companion. Things get more complicated yet with the rather fey devil himself ("Peter Pan, Antichrist.") attempting to collect Pendragon's soul, and then Quintus manages to travel back into the past himself ("I've come to show you the miracle of mylar!"), arriving naked save for his watch and immediately mugging a knight for his armour. However, it's worked out that if Helene is executed after all, all her future lives will cease to be, so she marches herself to the scaffold. Diana wakes up ("Oh, I had a horrible dream I wasn't a hooker!") reinvigorated, more articulate, and ready to turn over a new leaf, but Quintus is stuck in the past, his empty clothes left in Olinger's office.
With the "riffers" themselves making frequent comments about how confusing everything is, in some ways this episode is sort of overwhelming. At the same time, each individual moment isn't bad on its own. The "host segments" do feel particularly lengthy at times, though, perhaps reflecting how at the beginning of the "Sci-Fi Channel era" the Best Brains were being discouraged from filling out episodes with shorts. Things start off with what just might be a dig at the "plot arc" concept of the show at that point as Mike is encouraged to fill in more and more backstory. Then, with the Satellite of Love at this point held over the planet of the Observers (the Observer played by Bill Corbett who became a regular is sort of in the background, his brain tossed into what's either an "Enrichment Chamber" or a mini-fridge), everyone gets intelligence tests; Tom Servo "tests well" and briefly becomes an Observer himself. One last extended segment features Professor Bobo (who's by now basically fallen into his "big dumb ape" mode) making a late-night sandwich with great enthusiasm and slices of chilled brain. Even so, this prolonged exit might detract from the episode a little.