Sezon 5 serialu Arli$$ był emitowany na HBO od dimanche 4 juin 2000 do dimanche 3 septembre 2000. Składa się z 13 odcinków, z których pierwszy nosi nazwę "Creatures of Habit", a ostatni "You Can Pick Your Friends..."..
Comic actor Robert Wuhl, who created and stars, plays Arliss Michaels, a sports super-agent driven by twin motivations of profit and idealism. Arliss is in the race to realize his clients' dreams of stupendous wealth, but he's just as likely to put his reputation (and big bucks) on the line to help a fading player claim his niche in history. As with HBO's The Larry Sanders Show, Arli$$ gets a lot of mileage out of verisimilitude.