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UWS Prep School Grads are Rising Hip-Hop Stars

UPPER WEST SIDE — Graduates of the elite Collegiate School usually make their marks in finance, law, or politics.

But two recent alums are rising stars in a different specialty — hip-hop.

Doug Gleicher and Jesse Finkelstein, both 19, formed the duo Upper West in April 2011. On Feb. 28, they released their first mixtape, West Side Stories.

Riding a rising tide of internet buzz, the EP's first single, "West Side Story," has already been downloaded more than 10,000 times from MediaFire.

Gleicher and Finkelstein, who were both born and raised on the Upper West Side and attended Collegiate from kindergarten through 12th grade, pay tribute to their home turf with lyrics that reference Riverside Park and West End Avenue.

They've also shot music videos that feature local spots like West NYC shoe store on West 72nd Street.

But with catchy beats and samples from Beirut, Death Cab for Cutie, and Los Lonely Boys, their music has started to win a following beyond the 10023 zip code. On Saturday, they performed at the South by Southwest festival in Texas.

The group formed when Gleicher, a third baseman on Collegiate's baseball team, was trying to recover from mono in time for college baseball recruiting season his senior year.

Forced to sit still for hours at a time while an IV drip delivered Vitamin C to his system, Gleicher found himself suddenly writing songs to kill time.

"These lyrics just came to me," Gleicher said. "It was out of nowhere."

Though he had no connection to the military, his first song, "Nothing We Can Do," was about a soldier in Iraq missing his wife and child. His longtime friend Finkelstein, who grew up on West 84th Street and Riverside Drive, wrote music to go with it, and the two recorded the song at a friend's Upper West Side home recording studio.

They messaged the song to friends, and within weeks the music blog Good Music All Day contacted them, wanting to know why they didn't have a Facebook page, Gleicher said. They put one up and racked up 500 likes within a week, he said.

"(The song) circulated around the prep school scene, because this had never really happened before in our social circle, but then we started getting actual fans from around the country," said Gleicher, now a freshman at Washington University in St. Louis.

"Because of the feedback we got we decided to keep recording."

When they started getting inquiries about playing live, they turned to a Vassar College student who had started a talent management agency for help. Since then, Upper West has performed at boarding schools like Choate Rosemary Hall, Milton Academy and Avon Old Farms.

In August 2011, they played a sold-out show at The Canal Room in TriBeCa.

When the two took off for college — Finkelstein is at the University of Pennsylvania — the pair continued to record. Though they've been lumped in with "frat rap," Gleicher and Finkelstein like to call Upper West's sound "new age hip-pop," a reference to their clean, poppy sound.

"Our biggest draw is the catchiness of Jesse's beats," Gleicher said. "They get stuck in your head. We're not gritty."

Gleicher got his first exposure to rap when his godfather Eric Weinstein — Mark Wahlberg's longtime friend and the model for "E" on Entourage — would drive him around town in an Escalade blasting Tupac Shakur, he said.

"I was 7 or 8-years-old and I thought I was the man," Gleicher said.

Not too long after, he stumbled on a CD of 50 Cent's "Get Rich or Die Tryin'" and couldn't resist listening to it after he saw the parental advisory sticker warning of explicit lyrics.

"I'd never been exposed to that stuff," he said.

"It was vulgar, it was about killing, but the sound was amazing."

With his songs for Upper West, Gleicher said he strives for that same high-quality production value, but he and Finkelstein make no attempt to be gangsta. Instead, their songs have an almost earnest quality — "Home" talks about the joy of returning to the Upper West Side after being away.

"Rap nowadays is mostly people trying to talk about making money and getting ass and doing drugs and that's not what we're talking about," said Finkelstein, who also goes by the name Jesse Fink.

"We're actually writing songs that are stories, or have a meaning, or are something more than generic rap music."