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How do rock and roll bad boys stay relevant when they grow older and less dangerous?

The Rolling Stones no longer symbolize youthful rebellion and decadence as they did 50 years ago. So like a smart business that refines its brand, the Stones now focus on one core asset: their rock legacy. As the Rolling Stones celebrate their 50th anniversary with a limited-run tour that came to the United States December 8, the four principal band members (average age: 68) have assumed the role of the blues greats who inspired them to become the Rolling Stones in the first place:  playing their music onstage until they drop. And the Stones are innovating with digital technology to share that legacy. In doing so, the Rolling Stones provide a lesson for marketers on how to update your brand and find new ways to create a valuable audience experience.

The recent 50 and Counting Tour concerts in London and New York, drawing upon a catalog of songs such as “Gimme Shelter” and “Paint It, Black,” have reminded fans and critics of the band’s musical legacy. And you simply cannot overstate what the Stones have accomplished in their storied career. Especially in their first 10 years, the group created music that was by turns brutal, beautiful, threatening, and galvanizing. Their most well known songs and albums routinely rank near or at the top of critics’ lists of the greatest and most influential works in rock history.

But the Stones did more than make essential music when they first started recording bluesy singles in 1963: from the start, they were also rock’s original bad boys. In the early going, the band’s dirty and malevolent reputation was a product of the hype-making machinery of their brilliant, PR-savvy manager, Andrew Loog Oldham. Loog Oldham sought to portray the five Londoners as a grimy alternative to the cuddly Beatles from the burgeoning Liverpool music scene. “They don’t wash much and they aren’t all that keen on clothes,” he was fond of saying, even though Mick Jagger was a notoriously fussy dresser and Brian Jones washed his hair so often his nickname was “Mister Shampoo.”

But it didn’t take long for the Stones to create notoriety that has become the stuff of legend: numerous drug busts . . . womanizing . . . the notorious Altamont concert . . . generally speaking, enough debauchery and misbehavior to inspire generations of rockers ranging from Stevie Tyler to Axl Rose. Perhaps Keith Richards best summarized the ethos of the Stones in 1967, when, defending himself on the stand after the infamous Redlands drug bust, he proclaimed, “We are not old men. We are not worried about petty morals.”

But eventually the Stones outlived their mythology. By 1983, as the band members were pushing their 40s, rock critic Dave Marsh in The Rolling Stone Record Guide was talking not about the band’s notoriety but asking “whether rock’s most famous (did some say best?) group can survive to middle age” — and that was nearly 30 years ago. The Stones survived middle age and would go on to experience noteworthy achievements, as well as the harrowing setbacks that come with age. Keith Richards wrote a book, appeared in two Disney movies, and suffered a concussion when he fell out of a coconut tree at age 66. Mick Jagger was knighted at the age of 60. Charlie Watts survived a throat cancer scare. Ron Wood drifted in and out of alcohol rehab.

Meantime the Stones continued to make music, but no one really took the “rock and roll bad boy” image seriously anymore.  After all, Keith Richards was breaking his ribs reaching for a book in his personal library, and Charlie Watts joked about living a cushy life, touring only when he wanted to, not when he need money. By contrast, contemporaries Bob Dylan and Neil Young escaped the problem of “brand age” — Dylan because he set a pattern of constantly reinventing himself early on in his career, and Young because his image as a peace-loving, political hippie seemed timeless. No one was cracking wise with remarks like “Would you let your grandmother marry a Rolling Stone?” about Dylan or Young because they’d never been packaged as sexually dangerous when they were in their twenties.

By the 1990s and 2000s, the Rolling Stones were a far cry from “boys who any self-respecting mum would lock in the bathroom,” as the Daily Express described the band in 1965. So the Rolling Stones recast themselves as standard bearers of rock history. In the past 22 years, they have released just three albums of original music. Their most recent album, 2005’s A Bigger Bang, received generally good reviews and proved that the Stones still stand for great rock and roll when they want to create new songs. On the other hand, in the same time span, we’ve witnessed eight greatest hits albums from the band (consisting of five live albums and three studio singles collections), the unearthing of the 1960s concert The Rolling Stones Rock and Roll Circus, the re-issue of 1978’s Some Girls and 1972’s Exile on Main St., and most importantly, at least four highly lucrative global tours.

The 50th anniversary celebration is all about looking back: the release of yet another greatest hits package (with a few new songs tossed in), the publication of a lavishly illustrated history, an HBO documentary, a DVD about the band’s 1965 tour of Ireland, the band’s first-ever iPhone app (whose content emphasizes the band’s legacy), and, most significantly, the limited-run tour that has raised eyebrows for its expensive ticket prices. (It should be noted that the Stones will also appear on the 12-12-12 Benefit Concert for Hurricane Sandy relief — perhaps to offset the grumbling about the cost of paying to see the Stones) But, interestingly, the Stones are looking forward in a different way: through their use of technology to share their brand.

“The Rolling Stones are making waves in digital second screen entertainment,” crowed Mike Snider of USA Today on December 6, in describing an innovative streaming of the band’s December 15 concert. For the price of $39.95, fans can stream the Prudential Center concert on their personal computers, smart phones and tablets — an experience that will include interactive features such as  a Twitter feed. Digital ticket owners will be able to watch the concert as often they’d like on multiple devices for 30 days.

“This first-of-its-kind worldwide digital offering to mobile devices is a Stones’ streaming experiment that, if successful, could set a new industry precedent that brings a wave of live music to Net-connected portable,” Snider wrote.

The 50 and Counting Tour has met some criticism, with naysayers characterizing the band as “coasting on past glories” and a collection of “saggy, goulish flesh onstage” (as if the band had morphed into the zombies from The Walking Dead). But head Stones Mick Jagger and Keith Richards know that when your work includes classics like “Sympathy for the Devil,” “Under My Thumb,” and “Brown Sugar,” you are rock history. And apparently the Stones are still doing a credible job of making history come alive onstage. After their November 25 show in London, The Daily Mail‘s Jan Moir wrote, “You might imagine that they had been worn down by life, by wives, by arthritis, by scandals old and new, by drugs, but no – they seemed indestructible,” and Gregory Katz of The Huffington Post wrote, “The verdict is in: The Rolling Stones are back. They may look old, but they still sound young.” After the band’s December 8 show at Barclay’s Center in Brooklyn, Billboard magazine gushed that the Stones proved themselves to be a “powerful, primal, world-class rock band.”

The Rolling Stones have produced a body of work that they will play the hell out of while they are alive — music that will be interpreted by others for decades to come, just as the Stones themselves have celebrated and interpreted the music of blues giants like Howlin’ Wolf and Willie Dixon, and rock giant Chuck Berry, during the course of their career.

And by continuing to play their own standards, the band has elected to follow the example set by the blues greats in more ways than one: as Keith Richards has vowed, he’ll “do it like Muddy Waters — till I drop.” But unlike blues great Muddy Waters, the Rolling Stones have access to the digital technology that will stream their legacy.