35 Photos of John Mayer’s Journey From Boy-Next-Door to Wanton Sleazeball

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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

It's been a wild ride for Mr. John Mayer, the past decade or so. Besides Chris Brown, it's hard to find another male star who has experienced such an abrupt change of public image: The sensitive guitar man who once dreamed of nothing larger than running through the halls of his high school is now widely regarded as the most shameless cad in all of Hollywood.

On the occasion of Mayer's 35th birthday—the age, traditionally, when man-children have been forced to take stock of their lives and their choices—we run down exactly what happened in his transformation from fresh-faced Berklee dropout to unrepentant womanizer.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Mayer burst onto the scene looking very much like the music nerd he was: Bad glasses, worst posture and one serious case of Awkward Guitar-Face. All but one of these would eventually be fixed.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

With his wrinkled shirt and baggy olive pants, Mayer was not an especially savvy dresser even by the standards of the early '00s.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

However, he had already perfected what we call College Boyfriend Hair.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

This John Mayer was able to be friends with a woman without later telling everyone what his penis thought of her. Check out  the goofy hug he's sharing with Norah Jones!
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Early John was even a little nervous hanging out with all those superstars!
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Here he is showing off his best high-school prom style at the 2003 Grammys, where he won Best Male Pop Vocal Performance.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Who could say no to a face like this?
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Look at that hoodie—John Mayer was Mark Zuckerberg before Mark Zuckerberg was.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

We know, we know. A pink shirt? But don't worry, John wasn't going too crazy yet: His modesty was still protected by that trusty white undershirt.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Remember the suit-jacket-and-jeans look of the mid-2000s? Mid-period John Mayer was all over it.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

He also loved those velvet blazers that were popular for a hot minute.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Uh oh! The long hair, in retrospect, was our first sign of trouble.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

After all, nothing says "I am an artist and I demand to be taken seriously!" than a mane full of flowing locks.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

He was still safe enough, though, for you to leave your daughter around.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Not a good sign.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

This picture right here, this is the tipping point of John Mayer douchebaggery. The shirt is a little too unbuttoned, the hair is a little too stylishly tousled, the rock-star pose is a little too self-conscious. John Mayer could get less jerky after this moment, but he could never again go back to being the innocent music geek he was before.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

We don't want to analyze this body language too closely, but something is clearly going on with Mayer and Natasha Bedingfield in this photo. Did he feel the rain on her skin?
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

With fame and fortune assured, Mayer began to give himself more leeway to indulge his own ... appetites.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

And, right on schedule, we got our first hint of "I'm not the old me!" facial hair.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

All the love and affection of Mayer's Jessica Simpson period, summed up in one photograph.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Ugh.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

By 2007, Mayer had ditched the baggy button-ups for deep V-necks that emphasized his new physique. With the addition of tattoos and a chain, the look was complete.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Then came hipster scarves.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

And leather jackets.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

And sleeveless shirts.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Mayer's transformation was complete, but we just didn't know it yet; at the time, he seemed a fine candidate to escort an A-Lister to the Oscars.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

And no one gave a second thought to having him perform alongside teenage country superstars. It's not like he would seduce them and leave them brokenhearted or anything, right?
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

He's playing like he's joking, but you know that secretly John Mayer really just wanted to show off his abs.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

After weathering a scandal over his racist, sexist and just generally douchey comments in Playboy magazine, Mayer re-emerged in the public eye in summer 2010. For his big comeback look, Mayer aimed at nerdy contrition, but ended up dressing like an old guy from Caddyshack.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Mayer then entered what historians would later call his "Johnny Depp years."
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Seriously, the resemblance is uncanny.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

But then John Mayer discovered the love of his life, and everything changed. We're talking, of course, about that darned hat.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

The hat was late-period Mayer in a nutshell: Garish, pretentious, and frequently spotted in tabloids.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

And for some reason, he wore it everywhere.
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35 Photos of John Mayer's Journey From Boy-Next-Door to Wanton Sleazeball

Mayer's recently ditched the hat and cleaned up his shaggy mane. Could a 35th-birthday turnaround be in order? We'll have to wait and see.
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