Which Past Stars Would Make It In Today's Environment? A Thought Experiment

So you may not know this, but Dolly Parton’s arms are covered in tattoos – full arm sleeves.  And, it is said, her breasts are also covered in tats.  She merely covers them up in public because, well… I suspect it’s because back when she started her career, no nice young girl had tattoos.
Just another way Dolly Parton was ahead of her time.  Dolly’s one of the smartest recording artists out there – a sharp songwriter, an above-the-curve businesswoman, and the kind of feminist who reconciled her sexuality with her talent in such a casual way that she slipped under the goddamned radar for most people.
And I think about Scalzi’s post on Heinlein yesterday, where he tore apart the yahoos who said that Heinlein would never be nominated for a Hugo today by pointing out that Heinlein was, above all, a commercial writer.  He adapted his style to write for the highest-paying markets, paving the way for “mainstream” sci-fi, and if he were to start today as a young Heinlein with his talent, he’d doubtlessly be cranking out respected bestsellers.
Dolly Parton starting today?  This is the woman who wrote classic songs like “Jolene” and “Greatest Love of All,” and writes a song every day – and at least some of those songs would, with today’s modern folk renaissance, still be great hits.  She’d be openly tattooed, still a sex symbol, and probably more conflicted about her evangelical Christianity, but plop Dolly into this musical environment and I still think she’d make it to the top.
But you know who wouldn’t be a star?
Michael Jackson.
Not that Michael wouldn’t still be magnificently talented, but he got his start in the Jackson Five.  When was the last time you saw a family act hit the top of the pop charts?  Or a kid on vocals?  Hell, we still talk about how fucking weird it is to like MMmmmBop, which just shows how much of an outlier that is. A lot of Michael’s talent was developed while he was doing the touring thing with his family, and I can’t see The Jackson Five making the charts.
No, if you’re a kid these days, you do the Disney school of pop star, and not only is Disney not particularly great at promoting black kids as their marquee idols, I don’t think Michael’s controlling father would have let him go.  So Michael Jackson would vanish, and probably be a lot happier somewhere, and most likely alive.
What about the Beatles?  Proooobably.  The interesting thing about the Beatles is that they were the first teen pop stars of such a magnitude, and unlike the teen idols to come later, nobody shaped them – they just sort of started wearing those crazy haircuts on their own.  Unlike, say, One Direction, nobody said “Let’s put four cute boys in a band and have them perform hits,” the Beatles just sort of organically arose – and that’s what enabled them to make the transition from the Backstreet Boys of the 1960s and into the fucking Beatles we know today.
I think if the Beatles had somehow assembled themselves today, they’d be much more managed – with a cadre of people trying to mold them to be more popular, discouraging them from taking risks, promoting and actually fragmenting the band in different ways.  I think the Beatles would still be popular in that Hanson sort of way, but the likelihood of them being left alone to actually evolve into the magnificence of what they became would be very small.  I think the Beatles’ Hits would be four or five chart-topping singles after a good showing on a few reality shows, and then too many agents trying to steer them in bad directions.
So that’s the theory.  Question is, what great singer from the past do you think would succeed or fail today thanks to various marketplace changes, and why do you think they’d still triumph, or meet an ignominious defeat?  (Bonus points if you can pick someone obscure who would catch fire in today’s record market.)