Arriving at the Los Angeles home of former ’90s boy band singer Robbie Williams in early 2008, journalist and author Jon Ronson was greeted by a bearded and bulky version of the Brit, who had invited Ronson to join him on a trip to the International UFO Congress, which was taking place at an unglamorous casino resort in Laughlin, Nevada. A decade prior, Williams’ was in the ascendant on the back of “Angels” in his home country, where he and songwriting partner Guy Chambers were soon to compose another surefire hit, “Millennium.” Now here he was, spending a sunny LA day watching alien DVDs with the curtains drawn. Yet this was not a case of pop ambition gone to pasture. The intervening years had been wildly successful for Williams, who was, and remains, famous around the world. Everywhere except for America, still, although two of his three current luxury homes are located in LA and Malibu.

The scene of reclusion Ronson walked into was real enough, but only captured one facet of Williams’ situation at that time. Reading fantastical stories about extraterrestrials provided a necessary diversion from reading fantastical stories about himself in the tabloids. He had in the previous year attempted to take something of a respite from the non-stop momentum, but he hadn’t scrapped the lifestyle; a private jet was hired to fly them to the Laughlin convention. “Robbie Williams is, as Keith Richards said of Mick Jagger, ‘a great bunch of guys,'” wrote Caitlin Moran in 2005. Multiple personalities regularly rubbed elbows in interviews with Williams, particularly back in the ’90s, but underneath the impulsive behavior and urge to give a good quote, a more calculating mind may have been turning.

Asked in 2003 how important it was to him to have a hit record in the US, Williams answered, “I go back and forth on it. This morning I was done with it all. It’s a lot of work and stress.” The effort required to reach the level he already enjoyed on other continents was one consideration for Williams, as well as for those counting on him. “He does between 5 and 6 million copies on every album without the United States,” said Tony Wadsworth, then chairman and CEO of EMI Music UK & Ireland, to Billboard in 2006. “So, does he need the States? From a strictly business point of view, I would say the answer is ‘no.'” The implication was that Williams was “deliberately choosing to concentrate on other territories,” but after nearly a decade of the press wondering when he was finally going to break America, an answer was needed — even if that answer was ‘maybe never, and that’s OK.’

Robbie Williams was as likely and unlikely a pop star as any. Born in Stoke-On-Trent, a city something like England’s own Cleveland, his father was a regional comedian and singer and his mother was a florist. Divorced when he was three years old, both could see their son was a natural performer. Williams’ fortunes changed forever when he was 16 and his mother, Jan, saw an advertisement in the local paper for a boy band audition. That was in 1990, and the upstart ensemble soon solidified under the name Take That.

Five years later, he was being told to rein in his growing penchant for partying or lose his job. Williams told The Face that fall that he had wanted to stay in the group until the end of the year, after their first tour beyond Europe when his contract would be up, but that the other four had confronted him and asked him to leave before the tour. The timing was unfortunate for both sides.

Take That were at the height of their popularity when Williams was cut loose, and though he now had plenty of time to indulge in his other interests, he also had to figure out what to do with his new life outside the bubble at the young age of 21. Take That still had Gary Barlow, their central songwriter and lead singer, as well as the other three blokes (Howard Donald, Mark Owen, and Jason Orange), but they turned out to be no less compromised by the rearrangement. They finished the tour for Nobody Else, their third album, but afterward the quartet decided they were finished as well.

“Back For Good” was an ironic title for a song that would turn out to be the first, last and only mark Take That would make in the US. In 1995, the nation was in the low ebb of its own 10-year boy-band cycle and had no need for a UK import. There was, though, a huge audience for R&B vocal groups, and “Back For Good” had enough heart and polish to pass muster with fans of acts like Boyz II Men (who recorded a cover of it in 2009). Nobody Else was released here in August that year, its cover already featuring just the four remaining members, even though as The Face pointed out somewhat conspiratorially, it “came out in the US weeks after Robbie’s departure.” “Back For Good” became a Top 10 hit that November, but there would be no capitalizing on the momentum.

One can catch glances of Williams’ bucking against Take That’s squeaky clean constraints in the “Back For Good” video, a delightfully dated black-and-white bit of slow-mo dancing in expensive furs under stage rain. In it, the fresh-faced newjack who was found singing lead and stealing the spotlight in the “Everything Changes” video only two years earlier has become stubbly, shorn of fringe, and is projecting as much of a rough edge as the puppet masters would presumably allow. Williams appears to be attempting the impossible in a boy band: changing his character.

“Just like the Beatles in their teenybop prime in the ’60s, [Take That] had to have their own ‘personalities’ glued on to their chiseled faces,” observes music journalist John Robb. “They had a cute one (Mark), a grunge one (Howard), and one that could dance and was a bit street (Jason…) and a daft one (Robbie).” The Face tried to assert in their post-breakup profile that Robbie “was always the cool one in Take That,” but Robb was not the only one who clocked him as the comedian of the gang; Williams even characterized himself as such. “I spent six years in Take That and every interview I said nothing apart from the odd witty comment,” he said.

Take That were blatantly modeled after New Kids On The Block, but NKOTB did not also provide a template for subsequent individual careers. Gary Barlow was the horse to bet on, and his solo pivot in the UK began strong with a few well received if anodyne adult contemporary hits in 1996 and 1997. Williams, meanwhile, got off to a less auspicious start with a cover of George Michael’s “Freedom,” a too-obvious choice that, then being only six years old, wasn’t in need of reviving, and to which Williams added nothing new but himself. Commercially speaking, “Freedom” and his next few singles fared decently in the UK charts, but the perception of Williams as a burnt-out party boy persisted until “Angels” took on a life of its own at the end of 1997, at which point Williams eclipsed Barlow for good.

There was nothing really new about “Angels,” a piano-led ballad in the vein of vintage Elton John with a drum-boosted chorus, but Williams did stumble into a kind of innovation. Similar to the way Alanis Morissette had then recently found the middle ground between alt-rock and pop, Williams took the sound of the Britpop guitar bands he wished he could be in and refitted it for his mainstream-honed voice. Much had been made of his visit to the Glastonbury Festival in the summer of 1995, where he was introduced to Oasis and even came on stage for a minute to jokingly dance with them during “Shakermaker.” The episode likely hastened his exit from Take That, but Williams was taking notes.

“Britpop? It’s great! Great bands and I’m mad for any British youth movement,” Williams told the Guardian at the end of that year. “I’ve discovered guitar bands,” he went on. “I used to think indie music was a bunch of miserable people complaining, and because I was in Take That I thought that everybody had to be happy, and every message should be about love. But this year I’ve realised that the indie attitude’s right.”

Bolstered by his arranged creative marriage to the classically trained former World Party member Guy Chambers, Williams took to Britpop with aplomb. “We’ve always tried to plunder the best bits of modern music,” Chambers was quoted as saying of his and Williams’ songwriting approach in the Independent in 2000. If Noel Gallagher and others around him could borrow from the best bits of UK rock from previous generations, surely they could repurpose that indie present for broader appeal. They more or less did just that on Life Thru A Lens, Williams’ 1997 debut album, and after a slow-ish start the strategy paid off big time in Cool Britannia.

“The combination of Chambers’ musical chops and Williams’ playful, pop-culture-splattered lyrics was perfect. Eighties-throwback pop-rock filtered through the Britpop of bands such as Blur and Pulp…” the Independent stated. Indeed, those lyrics showed another way that hanging around with the Gallagher brothers was rubbing off on Williams. “Mad for it” was but one Manchester-ism spouted ad nauseam by Oasis and their ilk at the time that he picked up.

“Come and have a go/ If you think/ You are hard enough” Williams repeats over the middle eight of “Millennium,” the first single from I’ve Been Expecting You, his 1998 sophomore album. It’s a funny time and place to issue such a challenge to no one in particular, especially in close falsetto, but it’s hard to dispute the swagger he must have been feeling in the studio as the song was coming together. There was also precedent for the line: former Happy Mondays leader Shaun Ryder had made the same declaration on the track “Shake Well Before Opening” from Black Grape’s 1995 debut album, It’s Great When You’re Straight…Yeah. “Millennium” did not pay homage to either Oasis or Black Grape, but it was pretty clearly Chambers and Williams’ stab at their own “Bitter Sweet Symphony.”

The Verve’s 1997 single was a no-brainer candidate for emulation; an international smash by a band with real rock cred. Plus, by the time “Millennium” was first released in the UK in September of 1998, the Verve were already hurtling toward their second demise. Chambers and Williams may have even learned from the mistakes of “Bitter Sweet Symphony,” ordering up an approximation of the strings from the James Bond theme “You Only Live Twice” instead of directly sampling anyone who might potentially be litigious. Lyrically, Williams stuck close to Verve singer Richard Ashcroft’s theme of fatalism, but “…we’ve been making money since the day that we were born” was a bit more rousing than “You’re a slave to money then you die.”

Beyond the qualities of the tunes themselves, it was Williams’ personality that carried his music to millions. In the “Millennium” video he’s dressed up like 007 (as he also is on the cover of I’ve Been Expecting You) and mugging for the camera in almost every shot. His extracurricular antics in the waning days of Take That may have hurt his reputation, but everyone loves a comeback kid. “In the tradition of great artists, Robbie’s more than a record,” Capitol Records then-president Roy Lott was quoted as saying in Entertainment Weekly in 1999. “He’s the whole package.” In 1999 it was finally time to take that package to America, and expectations were high. “Everybody who’s seen one of his American showcases or big shows in Europe has been like, ‘This is it. This is the guy’,” said MTV’s Lewis Largent in that same EW article.

Almost nothing was left to chance. Williams’ first performances were showcases for the media and music industry, not smaller club gigs. Neither Life Thru A Lens nor I’ve Been Expecting You would be released in the States. Instead, tracks from both would be put together on a compilation called The Ego Has Landed which would serve as his American debut. Ego thus boasted “Millennium” and “Angels,” as well as “Lazy Days,” “No Regrets” — featuring not one but two pop Neil’s, Tennant of the Pet Shop Boys and Hannon of the Divine Comedy — and other Williams-Chambers numbers that had the most crossover potential.

The Ego Has Landed landed on these shores in early May of 1999, but the rollout extended through the year. “Millennium” was the lead single and received solid radio airplay and a “Buzzworthy” designation on MTV. Even the rock-leaning Rolling Stone conceded that Williams could be “a turn-of-the-century Tom Jones.” “Millennium” charted but it didn’t make serious waves. Heads were scratched. “Angels” was released as the second single that fall, and achieved more or less the same. Music industry insiders and the journalists who cover them would spend much of the 2000s trying to figure out why, and how to correct the problem.

Williams gave his own take on the matter four years later. “My sense of humor is very British,” he said. “Maybe my writing is too colloquial. Or perhaps Americans simply don’t like me.” Was it really all down to Bob from Stoke bidding unknowing Yankees to “come and have a go” and “have a jolly good time”? A Village Voice review from 2001 of Sing When You’re Winning, his third album, posited that the problem was a combination of Williams “rapping all comic and Cockney” and Americans being “most fascinated by British pop when it presents a mirror image of American pop.”

Williams also noted the sheer size of the country and the ambition it takes to turn heads from California to the New York Island, and came across as almost content that The Ego Has Landed had managed to go gold in the US. Williams had built a good following in the gay community and among Anglophile pop fans, perhaps that and mega-fame elsewhere was enough? It seemed enough for EMI, who in October of 2002 signed Williams to a global contract worth what was variously reported at the time as either $80 million dollars or up to £80 million pounds. “Despite past difficulties reaching an audience in the United States, Mr. Williams’s popularity in Europe has led EMI to make him one of the highest-paid artists in the music industry,” wrote the New York Times in May of 2003.

According to the BBC, the deal gave EMI “an unusually high share of profit from touring, publishing profits and merchandise,” but that didn’t mean the stakes were lowered — except for maybe in the States. “The deal was done based on my international success, excluding America,” Williams told Billboard. He expressed hope that his then-latest album, Escapology, would attain gold status in the US, but to date that hasn’t panned out. Escapology was solid, but it didn’t have anything as immediate on it as Sing When You’re Winning did with “Rock DJ,” and even that single had gone over American heads in 2000 despite its absurd strip tease/skin tease music video, which was state-of-the-art for its time and is still genuinely kinda messed up.

The determination to be the “edgy one” appeared to still fuel Williams even at this assured point in his career. Musically, Escapology had a mature MOR sound, but lead single “Feel” bared thoughts such as “I don’t wanna die/ But I ain’t keen on living either,” while “Come Undone” had risque lyrics and a controversial video to match. Given that his personal struggles were often the subject of tabloid entertainment, such bracing candor in his work was justifiable (and had long been part of his charm), but this also marked the point when Williams and Chambers fell out professionally and Williams took things further in his own direction. His next studio album, Intensive Care in 2005, was recorded but not released in the US.

It might sound glib, but there’s an argument to be made that Robbie Williams was, in a way, ahead of his time here. When America was finally ready again for a group like Take That, the Backstreet Boys and ‘N Sync cashed in. When America was finally ready for someone like Robbie Williams, there was Justin Timberlake, whose solo arc appeared novel only because most of us hadn’t been paying attention to Robbie’s own. We slept on “Rock DJ” in 2000 but woke up in time for “Rock Your Body” in 2003 instead. Whether it was because he dropped his aitches or didn’t drop everything else to focus on Stateside sales, ultimately he’s done fine without a platinum certification from the RIAA. Who has missed out on who remains the question.