Uptown, where the clothes do not matter
On 15 June 1993 Prince tracked Calhoun Square at Paisley Park in Chanhassen. The day before, the same room had cut The Ride, Poorgoo, a version of Honky Tonk Women, Bambi, Zannalee, The Undertaker and Dolphin, the batch meant for an album called The Undertaker that was then dropped. Calhoun Square was not part of that project. He was recording under the love symbol, not the name Prince. He sang and played guitar. Michael B. played drums, Sonny T. played bass, and Tommy Barbarella and Mr. Hayes played keyboards.
The title is a place. Calhoun Square was the shopping center in Uptown Minneapolis, at Lake Street and Hennepin Avenue, the district he had used as a lyric setting since Uptown. The song is an invitation. Meet me there. Clothes and hair do not matter. If you are freaky, they do not stare. On the 1998 booklet the four players are credited with supplying the funk, and his guitar and claves are credited, deadpan, to “Yo Grandma!” The track runs 4:46.
It did not come out in 1993. The first release was 29 January 1998, track three on disc two of the Crystal Ball mail-order box on NPG Records. He had already played it. The first known performance was the morning show on 28 August 1993 at Terminal 2 in Munich. MTV News used about 45 seconds. He brought it back only now and then, in 1993, then in 2002, 2006 and 2007. On 2 December 2011 at the Bell Centre in Montreal he sang it as Montreal Square.
It don’t matter clothes you are wearing or your hair. If you are freaky, they don’t care and they don’t stare.
(Prince, Calhoun Square)

The 1998 box is a vault dump, two eras jammed together, roughly 1985-86 and 1993-96, with Cloreen Bacon Skin from March 1983 as the outlier. PrinceVault lists no regular tour for Calhoun Square, only those occasional dates. Calhoun Square belongs to the 1993 half: the New Power Generation in the room, not the Galpin years of the title track on disc one. Retail copies of the box, from 3 March 1998, kept the song. Nothing on it was rebuilt for the package.
On 5 April 2019, at a Minnesota Timberwolves game in the Target Center, attendees received a posthumous 7-inch of Rock ‘N’ Roll Is Alive! (And It Lives In Minneapolis) with Calhoun Square on the B-side. The A-side answers Lenny Kravitz. The B-side is still the 15 June 1993 Paisley Park take, pointing at a mall in Uptown. The recording that counts is that one, with Michael B., Sonny T., Barbarella and Hayes, before the box and long before the basketball single.