If ever someone needed to ditch an old personal brand and start from scratch with a new one, it was 16-year-old Alfred Yankovic, an introverted college freshman who had spent most of his sheltered childhood alone in his room playing the accordion.

After skipping three grades along the way, Yankovic—you know him as Weird Al Yankovic—wound up as a teenage outcast at California Polytechnic State University—pining to be one of the cool kids on campus but never being able to pull that off.

He tried. Four hours away from his overprotective parents, he rebranded himself as “Al,” which, he assumed, sounded cooler than “Alfred.” He knew nobody, so nobody knew that he had been two years younger and twice as smart as most everyone in his ...

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