The Greatest TV Antiheroes of All-Time

“Give me a hero, and I’ll write you a tragedy.”

– F. Scott Fitzgerald

There’s an image of Tony Soprano, the patriarch of the North Jersey crime family, that is embedded into my brain: crouched in a swimming pool, gold necklace dangling around his neck, with a big cigar sticking out of his mouth, his cool, dark eyes are fixed upon us. They are taunting the viewer, as if to say, “Yeah, I’m the bad guy, but you’d trade places with me in a heartbeat.”

Truth be told, I’m not even entirely sure if the photo is meant to be a representation of the mafia don or a promotional photo of the actor James Gandolfini. Does it even matter? The two are now synonymous together. The fictional man who loved his family, but cheated on his wife and was a ruthless killer, who tried to get his head right by airing his dirty laundry to a shrink, brought on the era of TV’s antihero. The guy (or gal) you loved to hate.

For Gandolfini, it was the role he was destined to play. After many years of playing minor heavies (True Romance, Get Shorty), Gandolfini shot to stardom by showing a tender side to an otherwise despicable human being.

The Sopranos premiered on HBO in 1999, and since then audiences have had their fair share of irresistible TV antiheroes. These shows became mirrors for the turbulent times post-9/11, where even in our own government, heroes became hard to find.

These complex, morally ambiguous characters came one after another: Tony begat Vic Mackey of The Shield, who begat Don Draper of Mad Men, who begat the meth-king himself Walter White of Breaking Bad. These characters were most often men with insatiable desires, willing to risk life and limb to obtain whatever they felt was owed to them. Over the past few years, female characters began to show their corrupt colors, whether it’s PTA soccer mom-turned-weed dealer Nancy Botwin (Mary-Louise Parker) on Weeds, to Glenn Close’s ruthless attorney Patty Hewes in Damages. Family, it seems, is one of the few links between characters as desperate as Draper, White and Botwin.

“If any new or relatively new story factor is significant here, I think it’s the addition of family context, whether blood family or family by choice,” says Leo Baundy, professor of English and American Literature at the University of Southern California. “The Sopranos comes directly out of The Godfather, where whatever the evils of the Corleones, they are a family preferable to the impersonal corruption of politicians and government, and more relatable to the audience. It’s a kind of emotional enticement akin to Marvel’s fallible superheroes, or the X-Men villains (and heroes) with horrible childhoods. Even Ted Lasso, in the second season, is revealed to have a back story that makes [Ted’s] affability not so innate.”

As streaming services grew, and movies dwindled, audiences became increasingly OK with following a protagonist who held few qualms about showing their sinister side. For writers and showrunners, this allowed total freedom with storylines; they were no longer held to the principle that the viewers had to “root for” the good guy.

“TV was finally fully emerging as a serious art form in the U.S. by the 1990s, thanks to the expanded possibilities of cable and then streaming,” says Robert J. Thompson, professor of Television and Pop Culture at Syracuse University. “Broadcast TV once had to be appropriate for EVERYONE — talking horses, flying nuns, doctors who made house calls, etc. Literature has been filled with ambiguous characters, from Achilles to Macbeth to Crime and Punishment. TV began to catch up with the likes of Tony Soprano, Walter White and Don Draper.”

To celebrate the 15th anniversary of the last episode of The Sopranos (June 10, 2007), SPIN takes a look at the greatest TV antiheroes. Let the debate begin.

Walter White | Breaking Bad

After his stint as an executive producer on X-Files came to an end, Vince Gilligan felt bereft of ideas. Telling Vanity Fair in 2010: “[A friend and I] were just joking around on the phone about what we should do next: Should we be greeters at Wal-Mart? Should we put a meth lab in the back of an RV and cook meth and drive around the southwest? And that image…I don’t know, it just stuck with me.”

Walter White’s evolution from a family man desperate to provide for his family to the meth kingpin of the Southwest had audiences…well, addicted. Walter White found meaning in his own life by destroying the lives of others. They don’t get more antihero than that.