Madonna

You’d think that being the primary frontman of a boyband would be an excellent platform for solo superstardom. After all, it’s your voice on all those hit singles and your face getting the most screen-time in music videos. Indeed, Jackson Five frontman Michael Jackson and NSYNC co-lead singer Justin Timberlake were able to parlay their group dominance into individual success. If you consider Wham! to be a boy band (I’m not sure, to be honest), then George Michael is another example.

But others weren’t able to find much success outside of their groups. Ralph Tresvant sang lead on most of New Edition’s hit singles, but only managed two hits on his own. That was one better than either Jordan Knight of New Kids on the Block or Nick Lachey of 98 Degrees managed outside of their popular groups. And, of course, we’ve covered NSYNC co-leader J.C. Chasez’s solo debut album, which flopped so badly it ended his bid for stardom before it really began.

Then there’s the curious case of Gary Barlow. The Take That frontman was a fantastic singer who sang lead on almost all of his band’s songs. And whereas most boybands relied on outside songwriters, Barlow wrote or co-wrote nine Top 10 UK hits, including five #1 singles, during the band’s initial run from 1991 to 1996. When he went solo in 1996, the British media immediately anointed him as the next George Michael. Success was not only expected, it was preordained.

As such, that only made what eventually happened all the more shocking. In 2000, barely four years after Take That’s breakup, Barlow suffered the ignominy of being dropped by his label, all but ending his solo career. Worse, he had to watch as bandmate-turned-nemesis Robbie Williams wrote songs attacking him and making fun of his misfortune en route to becoming one of the best-selling artists in the world.

Where did it all go wrong? It started with his second album, Twelve Months, Eleven Days.