Achtung Baby saw Bono hiding behind several characters, including Judas in the album’s standout track “Until The End Of The World,” and later on the Zoo TV Tour as MacPhisto, a devil in a gold lamé suit on “Ultraviolet (Light My Way).” Bono, once synonymous with moral earnestness, was now dressing up as an aging, glam-rock Satan, delivering tongue-in-cheek monologues and singing Elvis songs. There was also Mirror Ball Man, a parody of American greed dressed up as a Southern good ol’ boy. Along with The Fly, these outsized personae gave Bono license to get his messages across without getting preachy: Shows ended with these characters making crank calls to local politicians and the White House, offering them the devil’s compliments. Whereas the Bono of old would have turned to speechifying, he was now getting the same point across—and more effectively—through sarcasm.

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Not that the shows were free of overtly sincere political moments. As the tour rolled on, Bono became concerned with the human drama unfolding in Sarajevo, which was being devastated by the Bosnian War. To bring attention to their plight, the band would stop mid-concert for a live, unscripted interview via satellite, where Bosnians would speak directly to Bono and the audience. It was “excruciating,” Mullen would later remark, “like throwing a bucket of cold water over everybody.” But while it attracted plenty of controversy over the ethics of making human suffering just part of the show, the stunt was thematically in line with Zoo TV’s overarching message about the blurred lines between tragedy and entertainment, and jarringly effective in highlighting that detachment.

The Zoo TV Tour ran 157 shows over 21 months, and its creative and commercial success coronated U2 as a stadium act for the next quarter century, forcing it to create bigger and bigger spectacles with each iteration. While U2 would briefly become even weirder and more conceptual for its two follow-up records, Zooropa and Pop, it was always Achtung Baby’s equilibrium between experimentalism and emotional accessibility the band was chasing, eventually finding it again on 2009’s No Line On The Horizon. It remains that way to this day, where each new album is measured against Achtung Baby as often, if not more so, than The Joshua Tree. It’s the album that cemented U2 as a creative force, even if nothing since has topped it.

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It‘s also the album that cemented the world’s collective image of Bono as the preening, sunglasses-and-leather-jacket-donning rock star—an image he may have adopted ironically, but that has now become inseparable from his real persona. And as such, it’s possible it’s made his slipping back into open, unironic activism slightly harder to take seriously, even as the smash success of Achtung Baby has given him a much stronger (and more forgiving) platform to stump for people like Aung San Suu Kyi, Nelson Mandela, and the latest repressed dissident du jour.

In the years since Zoo TV, to name just two such events, U2 headlined the Tibetan Freedom Concert in New York City and played the Super Bowl only months after the 9/11 attacks, where they projected the names of the deceased while playing “Where The Streets Have No Name.” These were weighty political moments, but few would say the band came off as proselytizing or mawkish during them. If pre-Achtung Baby U2 were subversive fist-pumping agitators, the U2 we’ve come to know since is more like a group of billionaire philanthropists—using their wealth and celebrity to propagate good in the world, but always with the inescapable air of condescension that comes from being lectured by the upper crust.

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Of course, it’s always a balancing act between pretense and cool, a fine line that separates taking rock stars seriously from rolling our eyes. For every ONE campaign that tangibly helps eradicate poverty and inequality in Africa, there’s a Glamour article naming Bono among its Women Of The Year. Speaking personally, I find the band’s onstage pontification on global poverty a bit heavy-handed, particularly at $150 a ticket. But on Achtung Baby, the band briefly found that balance, masking its pleas for hope and change behind a sexy, fatalistic veneer that made them far more attractive. As the album reminds us, a conscience can sometimes be a pest, love is blindness, and you’re better off letting go of the steering wheel.