We start off with a flashback to 1983, where we see just what a bad influence "Uncle" Jerry (Lithgow in full-on roadie mode) was on a curly-haired, six-year-old Barney. Not only did Jerry teach him magic, and the phrase "legendary" (kinda), he also imparted his motto: "Never stop partying." In the present day, Barney is still disappointed in his lame dad, so when he rebuffs an offer from Jerry to go on a fishing trip, Jerry tries to explain himself, saying that there comes a time when you simply have to stop partying, Barney decides to show him that continuing to party into old age is, in fact, a good idea.
To make the evening more party-like, Barney assigns everyone new identities. Marshall is now a playwright, and is in an open marriage with Lily. Robin is now a scotch-taster, and is still dating Ted, who is not allowed to talk about things that are boring. After an elaborate "Who's On First?"-style verbal game about nightclub names (including Where, Focus, Wrong, Was, Closed, Okay, Lame and Third Base), the gang ends up at Hopeless, where Jerry decides to give Barney what he wants: Crazy Jerry. After a few shots, he's dancing up a storm (and making Footloose references), and he and Barney take the party to the streets, where a series of drunken misadventures land them in police custody.
Back at the club, Robin spots her secret crush (Michael Trucco), a guy whose clothing she insulted a few years ago. After Ted Mos-blocks her by playing the faux boyfriend, they realize she first met the guy when she was still dating Ted -- in fact, it was the day he bought the infamous red boots -- and that she fantasized about him later that night while having sex with Ted. Furious, Ted announces their engagement to the room, further discouraging the crush. But we get a glimpse of the crush again at the end, in which Future Ted says it's not over.
Also, playwright Marshall and fashion editor Lily decide to put their fake open marriage to the test to see who can get more phone numbers. They make their usual bet, which is that the winner gets to have sex in the bathroom with the loser. Don't think about it too hard.
Sitting on the curb in handcuffs, Jerry reveals to Barney that he isn't drunk -- he magician-faked doing the shots, then drank milk from a paper bag, making an actually drunk Barney believe that he was fighting a biker (it was a mannequin), uprooting a parking meter (it was… lying in the street?) and vomiting on police cars (it was Barney). While the lesson of partying is lost on Barney, the fact that Jerry lied to him all night is not, and Barney is oddly touched. Luckily, they're both magicians, so they ditch their cuffs and make a break for it.
In order to make it home in time for the fishing trip with Jerry's son, they hitch a ride with one of Jerry's elderly driving students, during which Barney admits that he doesn't like his life, but he thinks he's too far gone. Jerry says he was further gone, and that Barney just needs to meet the right girl. Barney wonders if he already has. (Better hurry, dude -- apparently Trucco's coming back.) In the end tag, we cut to Barney, Jerry and Jerry's son in a boat in the middle of a lake. Barney: "This… suuuucks." Aaaaand scene.
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