Nathan Simmons, also known as Sliggitay, from his Facebook page

When Nathan Simmons graduated from Berkeley High School in 2003, he was lauded as an example of a student who seemed destined to go far.

Simmons had been a leader at Berkeley High. He played on the varsity basketball and tennis teams, took many AP classes, got mostly As, and served a semester as student body president. Half-white and half-black, Simmons had been selected by the administration to attend a conference in Cleveland Heights on the achievement gap, an appointment that garnered him mentions in the San Francisco Chronicle, the Daily Californian, and the Daily Planet.

And then there was his acceptance to Harvard.

“When I first got there I was on the Harvard trip — like, I’m gonna do this shit, I’m gonna get a great job, and I’m gonna be living my life,” Simmons told the East Bay Express in April. “Somewhere along the way, that changed.”

Simmons lasted about three years at the Ivy League institution, and in that time seemed to undergo a metamorphosis. Where he had once been the shining achiever, a large fish in a small pond, at Harvard he felt his urban roots keenly, according to what he told the Express. Instead of fitting in, he felt left out.

Simmons turned away from academics and towards another passion: music. He had become a rapper in high school, adopting the name Sliggitay (which means oral sex, according to the Urban Dictionary) and had his first hit while still in college, with a song that made fun of his black, upper class, third generation Harvard roommate. Then an arrest for drug possession (the charges were eventually dropped) and lewd public behavior hastened his exit from Harvard. He returned to the Bay Area and devoted himself to his music (while holding down a job in the molecular and cell biology department at Cal.)

His talent was noticed and he was mentioned along with other accomplished Berkeley rappers like Lil’ B and The Pack, The Cataracs, G-Eazy, Lyrics Born, YelaWolf, and others.

“Combining laid-back California drawl with the lightheartedness and soul of Southern rap, Slig is that rare artist that is equally enjoyable to listen to cruising through the town, sparking an L or at the club,” Andre David wrote on his blog, The Five and Dime Store. “Hailing from Berkeley, California, his rhymes have an unmistakable cadence and unique rhythm to them that separates him from the pack.”

By following more than 27,928 people on Twitter — and having an impressive 25,350 followers — and releasing his latest album, “The Mustache”, as a download in March, Simmons has continued to build on his music fame. (Even though the videos of his songs are so racy that they are not public.) Most of the songs “celebrate drug use and other vices in a not-very-subtle way,” according to the Express.

But, in late October, the rapper was arrested on charges of breaking into a home in San Francisco with the intent of raping a woman. Simmons, 26, who now lives in Piedmont, was arrested by police after allegedly breaking into a house in the south of Market area around 2:50 am on Oct. 30, according to police. A woman who was sleeping on a couch woke up to find a man standing over her, his pants down. The man pulled a blanket off the woman and she jumped up and screamed, prompting the man to run away.

The assailant had taken the woman’s iPhone and police were able to track it using GPS. They arrested Simmons in the 1600 block of Folsom Street.

Simmons has since pleaded not guilty to the charges and is being held on $1 million bail in San Francisco County jail, according to Bay City News.

His attorney, Charles Bourdon, declined to comment on the charges.

Frances Dinkelspiel, Berkeleyside and CItyside co-founder, is a journalist and author. Her first book, Towers of Gold: How One Jewish Immigrant Named Isaias Hellman...