“Winona” – Matthew Sweet

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To put Matthew Sweet’s paean to Winona Ryder from his breakthrough 1991 album “Girlfriend” in perspective, you must go back to 1989. It may be hard to believe these days, but at one point in the late 1980s/early 1990s, Winona Ryder was THE hot and very talented young actress of the day. While Julia Roberts got most of the mainstream buzz during that period, Ryder won the hearts of the hipster nerd crowd. And the movie that cemented this obsession was the 1989 film “Heathers.” Unlike other teen films of the era, “Heathers” was overtly nasty and cynical and seemed to make mincemeat of the John Hughes films that gained popularity during the 1980s. And Ryder, the star and heroine of “Heathers,” was the one hot girl of the era that hipster nerds thought they possibly might have a chance of charming. Never mind the fact that in real life Ryder dated Hollywood studs-du-jour Christian Slater and Johnny Depp (this was “21 Jump Street”-era Depp … long before he became … well … the Johnny Depp we all know and love today) and that she wouldn’t fart in our general direction even after consuming two beef burritos from Taco Bell, “Heathers” dammit … gave us hope … or at least played into our delusions that a very cute girl would embrace us outsider misanthropes.

Of course, if anyone had suggested back then that 25-years later Johnny Depp would be one of the biggest movie stars in the world, both loved by the critics and audiences and that Ryder would be relegated to barely noticed supporting roles, most would guffaw at the thought. But … that’s reality. Which is unfair to Ryder. She’s had her struggles over the years, but she’s still a damn fine actress. Her supporting turn in “Black Swan” in 2009 deserved an Oscar nod, but got lost in the buzz surrounding Natalie Portman’s and Mila Kunis’s performances.

In any case, Sweet’s ballad may seem a little silly today, but it’s an accurate reflection of the psychic crush many had on Ryder back in the day.

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“Evangeline” – Matthew Sweet

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From Sweet’s classic 1991 album “Girlfriend,” “Evangeline” is a terrific, crunchy, upbeat hard-rock love song. I’m not entirely sure who did the shredding guitar work on this song, but I believe it’s Sweet and Richard Lloyd (from the band Television). Sweet always had great taste in sidemen and production.

Arguably the best song ever written taking the perspective of a comic book character (Johnny Six from the 1980s comic “Evangeline”).