Season five picks up a few years after we last saw Hank Moody. He's living in New York and has moved on. After the unceremonious dumping of his latest girlfriend, Carrie, Hank's looking for a ticket out of town. Charlie calls with just such a ticket - a job on the Left Coast. Back in LA, Hank and Charlie drop in on the now-married Marcy and Stu Beggs. Stu rushes Hank off to a meeting with megarich hip-hop mogul Samurai Apocalypse.
Hank receives an unwelcomed surprise in the form of Carrie, ex-girlfriend. When Karen and Becca show up to invite Hank to a dinner party, he has no choice but to bring Carrie along. While Stu, Marcy and Bates' sex talk leaves the Van der Moody's searching for the nearest exit, the party gets out of control when Carrie makes a realization about Hank.
Charlie's boyhood dream is realized and Hank's worst nightmare comes true when Samurai Apocalypse invites the boys on a ride-along with the Santa Monica Police Department. While at a crowded Venice restaurant, Richard Bates hits the bottle, prompting a return engagement of the "Glorious Mangina."
It appears to be just like old times with Karen and Hank, but the moment is ruined by the arrival of a drunk Richard Bates. Hoping to save her from the misery of the situation, Hank quickly kicks Karen out of the house and takes off with Bates to piece together the events of the night before.
Hank finds himself stuck with the unpleasant task of reading Tyler's screenplay. Unfortunately for Hank, Tyler's hiding some talent under that head of hair. Even more unfortunate is the fact that the screenplay references Becca. Charlie and Lizzie's quadrilateral with Stu and Marcy heats up, but when MarStu's bedroom games hit too close to home for Charlie, it may be off to therapy for the four of them.
Hank, down an agent and best friend, finds reason to crash with his two favorite ladies -- Karen and Becca. There's still money to be made, so it's time for him to find new representation with Hollywood power agent Larry Levine. Lizzie's big break has arrived - a role in Santa Monica Cop, via a special favor from Stu Beggs. Charlie, distraught over his personal losses, seeks comfort from Marcy.
Hank has finally overstayed his welcome at the house of Karen and Richard Bates, so it's time to hit the road. But not before one last stop at Malibar, where he runs into Lizzie, who uses her newly acquired acting chops to lure him back to the Runkle Manor. Once there, Hank is surprised by everyone he loves and loathes - Karen, Becca, Charlie, Marcy, Stu, Bates and his creepy sponsor, Gabriel. Even Samurai Apocalypse and Kali show up. It's not a party until someone gets hurt. Luckily for these party-goers, Hank has it in him for one final run-in with Tyler.
Hank hits the local watering-hole, only something's amiss. Not only does Mr. Moody find himself surrounded by shadowy figures, but the bartender is an old, departed friend. Is Hank dreaming or has he finally made it to hell? Next it's onto the set of Santa Monica Cop where Sam's jealousy - and fondness for firearms - gives Charlie an opportunity to show just how much he loves his best friend and number one client. Later, Hank's ex-girlfriend surprises him with a way for them to be together forever.