Built circa 1940 next to the newly-built Hollywood Theater.
At some point prior to 1957, it was a soda shop/confectionary operated by Jeff and Ella Foushee. In 1957, it was Ben's Shoe Shine Parlor (and Clara's Beauty Nook), operated by Benjamin "Ben" N. Baldwin. In 1958 it was known as "Ben's Place," a soda/candy/hot dog shop mainly patronized by local teenagers.
Local resident and musician Doug Clark had this to say about the business: "...and next to [the Hollywood Theater], they had a place--Mr. Jeff Foushee and his wife...they had a place next to it, it was like a soda bar. You know, they sold soda and candies and all that. That’s where all the kids communicated after basketball practices and all, that’s where you went at night because Hollywood Grill and M&N Grill, that was more for the older guys because they were selling beer, but this place didn’t sell beer. That’s where everyone would congregate after basketball games, after football games, and all--at the theater which was right next door to Foushee’s. Okay but later on, Ben Baldwin’s, the Baldwins--they ran this place, and this is our place, with our soda shop for hot dogs, hamburgers, ice cream, and stuff like this, right on Franklin Street, right on the Carrboro line. This was your social life." (via fromtherockwall.org/oral-histories/doug-clark-on-the-hollywood-theater-oral-history-clip)
Other occupants of the structure/address (according to city directories; dates are approximate):
1959: Clara's Beauty Nook
1962-64: Carolina Mower Service
1965-70: Colonial Rug Cleaners
Its address since the 1970s/1980s has been incorporated into 409 E. Main Street, when all these structures were purchased and owned by the same family.
The Hollywood Theatre, October 1939 or April 1941 (screen shot from H. Lee Waters movie); the structure looks to be under construction to the left.
Sanborn map excerpt, December 1945
Ad from May 1958 (from the Lincoln Echo)
Former Hollywood Theater, circa 1975 (image via Chapel Hill Historical Society via Images of America - Carrboro); the business is at the extremem left of the photo
View east, December 2022 (via Google Streetview); the space with the map marker above its window is the location