To vote in this lineup, scroll to the poll at the bottom of the page, then head back to the bracket to see all of round two of The Best Pop Culture Dream Sequence, The A.V. Club’s no-holds-barred competition to see which dream sequence from TV or film deserves the title, “Greatest Of All Time.”
Mad Men dream sequences are often tormented, violent, and unnerving glimpses into the psyches of its characters. Not, however, Don Draper’s vision of Bert Cooper performing a song and dance number in socks to “The Best Things In Life Are Free” at the end of the seventh season episode “Waterloo.” Though brought on by Don’s grief, it’s bright and toe-tapping, both poignant and utterly fun. Don is escaping the staff meeting where Roger announces Bert’s death, when he hears his old boss’ voice call, “Don, my boy.” He launches into the tune a cappella, but is soon joined by a chorus of choreographed secretaries and a full score. When he’s done, Don is left holding back tears. Out of context, it’s a nod to actor Robert Morse’s legacy and the series’ ingenious casting: He was in the original Broadway production and the film version of How To Succeed In Business Without Really Trying. In the world of the Mad Men, it serves as a sweet send-off to the kooky ad man, while also speaking to the show’s persistent anxiety over the push and pull between financial success and unbridled creativity.
Throughout the run of The Sopranos, mob boss Tony (James Gandolfini) repeatedly edges toward psychological breakthrough, only to retreat and tamp it down beneath a blustering veneer of anger and resentment. Tony’s repression was such that, as the show would revisit again and again, the only place he could be truly honest with himself was in his dreams, where his deepest fears and desires were at last allowed to burble to the surface. The most effective of these many visions came in the second season’s “Funhouse,” where a food-poisoned Tony slowly awakens to the realization that his friend Big Pussy (Vincent Pastore) has turned FBI informant. Over a series of surreal vignettes on a desolate Asbury Park boardwalk, Tony processes those nagging suspicions as a terminal disease, as a comic Godfather reference, and finally, as a talking fish with Pussy’s voice, who flatly tells Tony what he already knows yet refuses to accept. Throughout these fevered hallucinations, the distant squeaking of a boat foreshadows the climactic moment Tony knows is coming—and that, as his dreams tell him, he can’t keep putting off. It’s strange and silly, yet laden with poignant symbolism, and the exemplar of the dream sequence’s unique power of revelation.