1. The Wire, 2002–08, HBO. The most sustained narrative in television history, The Wire used the drug trade in Baltimore, heavily researched by creator David Simon, to tell tales of race and class with unprecedented complexity. Politics, the war on drugs, labor unions, public education, the media—these were among the big themes, all examined through exquisitely drawn characters, such as the brilliant yet broken detective Jimmy McNulty (Dominic West) and the great avenging thug Omar Little (Michael K. Williams), who will live on in legend.
2. The Simpsons, 1989–present, FOX. It became the gold standard of the subversive dysfunctional-family comedy—animated or live-action—when the focus was shifted early on from punky son Bart to dad Homer, an id-driven but bighearted man-child whose IQ is inversely proportional to his cholesterol levels.
3. Seinfeld, 1990–98, NBC. Less the famous “show about nothing” than a show about the amusing, stressful, neurotic intricacies of friendship, Seinfeld converted Jerry Seinfeld’s observational stand-up routines into hilarious universal truths about the banality of life, value-added with catchphrases (not that there’s anything wrong with that). The most endlessly rewatchable sitcom since The Honeymooners.
4. The Mary Tyler Moore Show, 1970–77, CBS. Only the greatest, most detailed portrayal of a single career woman in TV history. With laughs and guts, MTM established the paradigm of “the workplace family.” Moore proved to be one of the medium’s finest straight-women as well as one of its most beautiful comedians.
5. The Sopranos, 1999–2007, HBO. David Chase’s landmark mobster drama introduced us to what has become a ubiquitous presence on TV: the antihero. Whether you rooted for Mob boss Tony Soprano (the fearsomely intense James Gandolfini) or against him, you couldn’t help but be riveted by him, no matter which family he was battling.
All-Time Greatest Albums:
1. Revolver, The Beatles, 1966. Not only did Revolver establish the enduring rules for long-players, it also conveyed the full narrative of the Beatles over 14 songs, from the hands-up garage jam “Taxman” to the sunny beach romp “Good Day Sunshine” to the churning psychedelic space walk that is “Tomorrow Never Knows.”
2. Purple Rain, Prince, 1984. Sexiest album ever? The PMRC thought so. The watchdog group was literally formed in response to this paisley-funk heavy breather, which builds to one awesome climax after another. How fitting that the movie the album was made for charts the Kid’s rise to fame: The moment Prince sang “Baby I’m a Star,” he was one.
3. Exile on Main Street, The Rolling Stones, 1972. Given the legendarily louche circumstances in which Exile on Main Street was made (heroin! French villa! More heroin!), it’s a miracle this double set of blues-, country-, and gospel-infused rock contains any great songs. In fact, they’re all great songs—even the one called “Turd on the Run.”
4. Thriller, Michael Jackson, 1982. If you grew up in the ’80s, this isn’t just an album; it’s the soundtrack to the first half of your life. Your first dance, your first summer romance, your first (and, rest assured, not your last) heartbreak. Thank you, Michael. Signed, everyone.
5. London Calling, The Clash, 1979. A lot of punks sneered about rebellion back then, but these boyos gave ’em a real revolution—musical and political—with the eternally urgent, genre-defying document that earned them the sobriquet the Only Band That Matters.
All-Time Greatest Novels:
1. Anna Karenina -- By Leo Tolstoy, 1878. A staggering novel about an unhappily married Russian aristocrat who chases what she thinks is love at the expense of everything and everyone else. Novelists generally embrace tragic lovers, but Tolstoy was too hardcore for that. Anna Karenina is both a cautionary tale and an exhortation to live our best lives. Anna Karenina is an immersive contemplation of the heart and the conscience. Long before Oprah praised the novel, Dostoevsky, Faulkner, and Nabokov knelt before it in awe. We do too.
2. The Great Gatsby -- By F. Scott Fitzgerald, 1925. You were probably forced to read it back when you were 16—but that’s not Fitzgerald’s fault. Give the novel another try. It’s an extraordinary feat of writing—sparse, cool, and elegant—as well as a riveting dissertation on the hollowness of the American dream as it played out during the champagne-fueled decadence of the Jazz Age.
3. Pride and Prejudice -- By Jane Austen, 1813. The courtship of the spirited, tart-tongued Elizabeth Bennet and the haughty Mr. Darcy is an enormously satisfying love story that still crackles. But what makes the novel truly sing is the deceptive grace of Austen’s prose as she limns the customs of her day with a sharp eye and a satirical wit. England comes alive through her wickedly smart drawing-room banter.
4. Great Expectations -- By Charles Dickens, 1861. London is depicted in every shade of the industrial spectrum, from gray to soot-black, through the eyes of a young ragamuffin yearning for a better life. It’s the greatest morality tale ever written—and the greatest soap opera, too.
5. One Hundred Years of Solitude -- By Gabriel García Márquez, 1967. A family saga entwined with the history of a village, García Márquez’s first masterpiece embraces all the big themes (love, war, death), deeply feeling the tragedy—and wisely seeing the comedy—of existence.
All-Time Greatest Plays:
1. Death of A Salesman -- By Arthur Miller, 1949. Over the past six decades, Miller’s drama about aging middleclass Everyman Willy Loman has become a classic evocation of the dark side of the American dream. Willy struggles to compete in an economy that prizes youth and innovation over old-fashioned relationships. Weighed down by disappointment and false pride, he sees little hope of redemption in his two underachieving sons, whom he’s taught to value superficial popularity over genuine accomplishment.
2. A Streetcar Named Desire -- By Tennessee Williams, 1947. Blanche DuBois, a fading Southern beauty with delusions of grandeur, may depend on the kindness of strangers—but she falls under the sway of her brutish, brooding brother-in-law Stanley Kowalski in Williams’ searing tragedy. Marlon Brando, mumble-mouthed and T-shirted, made an indelible impression as the first Stanley on stage and on film, but the role still packs a punch today.
3. Who’s Afraid of Virginia Woolf? -- By Edward Albee, 1962. The worst house party ever. In Albee’s explosive play, which returned to Broadway last fall in a Tony-winning revival, an embittered, long-married academic couple host a much younger prof and his wife for an evening of brandy and verbal abuse. The older pair are named George and Martha—making them the first couple of American dysfunction.
4. Long Day’s Journey Into Night -- By Eugene O’Neill, 1956. O’Neill recounts a fateful summer evening at the Tyrone family’s seaside home, where members of the clan battle their addictions (to alcohol and morphine) as well as one another.
5. Fences -- By August Wilson,1985. Wilson’s 1950s-set drama is a memorable portrait of Negro League ballplayer–turned–trash collector Troy Maxson. He’s a bundle of contradictions, demanding that his sons live practical, responsible lives even though he himself is a philanderer given to flights of fancy.