For much of 1995, Tupac Shakur languished in prison, his ascent into global celebrity temporarily put on hiatus. While in prison, one of the only creative outlets for Tupac was writing, something he did both religiously and prolifically. Offered here are six fascinating letters from Tupac, meant for a flame of his named Simi Chouhan, written and sent while Tupac was serving his jail sentence. These letters are fascinating, and provide incredible insight into the life and career of one of the greatest hip-hop artists in history. One letter, dated August 26th, 1995, details the rise of Tupac’s alter-ego, “Makaveli”. Tupac writes, “I’m just starting 2 read Machiavelli’s The Prince”. The idea of the Prince appealed to Tupac, who saw himself as both a ruthless figure and one to be admired, and loved, by his subjects. This letter is spread out over one and a half pages, and ends with the signoff, “Passionately / Tupac”. Written in blue and red ballpoint pen, both of these letters come with LOAs from JSA (Z42120 and Z42126).

     Another letter is titled “2Pac’s List of Tapes 2 Get & Listen 2 When U R ALONE”, and showcases Tupac’s varied musical tastes. The named albums are Jamiroquai’s “The Return of the Space Cowboy”, Counting Crows’ “August and Everything After”, “Wild Seed – Wild Flower” by Dionne Farris, Sarah McLoughlin’s “Fumbling Towards Ecstacy (sic)”, and Prince’s “The Hits/The b-sides 1, 2 & 3”. At the bottom of the letter, Tupac ends with “For the ideal results put all of these songs on one tape and enjoy. Think of Me! Tupac”. This letter, which is undated, comes with a LOA from JSA (Z42122).

     The final three letters are all poems written by Tupac, with the note “Exclusively 4 Simi from 2Pac”. They are titled “The Brightness of Your Smile”, “How Can [I]”, and “A Phrophecy [sic] of Passion”. The “I” in “How Can [I]” is a sketched eyeball, and the note to Simi is written as “Exclusively 4 Simi from Tupac Shakur”. Tupac signed each of these letters, writing “Thinking of U! / 2Pac” on each. These three letters each come with a LOA from JSA (Z42123, Z42124, Z42125).

     Finally, an envelope sent to “Ms. Simi Chouhan” of Los Angeles is included. Tupac wrote his name and address at Clinton Correctional Facility on the upper right hand corner. A Clinton Correctional Facility stamp is placed on the center of the envelope. This item comes with a LOA from JSA (Z42119). All of the pages are in fine condition and have been amazingly preserved.

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