Tupac Shakur

Courtesy the recipient

“U BETTER WRITE ME BACK! TODAY!!...TAKE YOUR TIME BUT HURRY UP!”

17-YEAR-OLD TUPAC SHAKUR SWEETLY TEASES COSIMA ABOUT HER NEWLY COMMITTED RELATIONSHIP

Writing Cosima as she begins to date Aaron—another student at Talampais High, the present letter catches a lighthearted Tupac up to the classic antics of a teenage boy. “I’m only writing you because I’m sure you’re bored,” he quips for an opener, continuing teasingly, “…So hows prison? Lonely?” With “prison” here being the confines of her newly committed relationship, Tupac gleefully ribs Cosima about how he hasn’t seen her much since she and Aaron made it official. While the other ‘Cosima Letters’ in this collection reveal the deep emotional sensitivity at the core of Tupac’s worldview, this lot is singular in its seven-line representation of the playful, clever sense of humor that charmed his friends and fans alike. Through an atypically explicit joke in Line 3, Tupac asks if Cosima and Aaron have been intimate, calling back to lot #101 sold in of Art and Influence of Hip Hop—the friends’ first discussion of her crush on their schoolmate. At that time advising Cosima to not let Aaron “have [her] ♥ until he earns it,” Tupac is now checking on whether her heart—and a bit more—have been earned. The boyish frankness of his inquiry simply represents just how close the friendship between Tupac and Cosima has become—he’s not afraid to banter with her around any topic, even the most sensitive. Missing the pre-Aaron frequency of their correspondence, Tupac implores, “Write me back so that I can have something 2 discuss. Answer my questions. Take your time but hurry up!! ☺.” Unable to resist one last laugh, Tupac ends by noting that he’ll “c [sic]” Cosima “at lunch on visiting hours.”

In the summer of 1988, 17-year-old Tupac Shakur and family moved from Baltimore to Marin City, California. There, Tupac attended Tamalpais High School in nearby Mill Valley, where he poured his creative energies into the award-winning, student-run Ensemble Theatre Company, and perhaps most importantly, The Microphone Sessions, a poetry workshop run by Leila Steinberg. Steinberg quickly recognized the future superstar's talent, and took him under her wing, mentoring his progress as a writer, and even welcoming Tupac into her family's home for a time. Their relationship would prove to be pivotal for Tupac's career—not only did Steinberg help Tupac hone his writing skills, but she would also become his first manager, organizing a concert for his rap group Strictly Dope, with whom Tupac recorded under the stage name MC New York. Steinberg helped broker Tupac's signing with Atron Gregory, manager of Digital Underground, and in 1990, Tupac joined the group as a roadie and back-up dancer, before going on to debut with them in 1991, under the stage name 2Pac. The rest is history.

Cosima, the recipient of the present letter, was a Sophomore and fellow member of the Ensemble Theatre Company at Tamalpais High. The pair shared a profound connection at this time, just before and in the beginning stages of Tupac's rise to fame, from their first meeting on Cosima's birthday in October 1988, and lasting for approximately 7-8 months. This, and the other letters offered (see lots 71-75) reveal a tender-hearted, fiercely passionate young man, dedicated to clear communication who loved people deeply, and expressed emotions without fear. Tupac’s ability to love so deeply, and to plainly express this love continues to explain the indelible mark he left on the hearts of those who knew him and devotees around the globe. These letters capture Tupac at a seminal juncture—an adolescent on the edge of true maturity, a natural wordsmith evolving into a lyricist and poet.