I'm not one for big chain retail stores, malls, etc. but I was a bit sad to hear that Sears is in trouble (again). I have a presentation that I give occasionally in my history of rock class about the role Sears played in the early days of popular music (well, and continued to play until recently...). When I first prepared my history of rock class, I was surprised at how often Sears came up in the most random places among the sources I was consulting. I must apologize--I'm writing this from a seven-year old PowerPoint slide show, and (bad scholar!) many of the references are long since missing and/or forgotten.
Sears was founded in 1886 when Richard Sears, a railroad agent in Minnesota, found a box of watches and started selling them to other agents. Around this time, farmers were selling their crops for cash and buying what they needed from local general stores. Sears (which became Sears, Roebuck & Co. in 1893) took advantage of the railroads and post office and leveraged their bulk buying power to save farmers money.
While Sears was initially sold only watches and jewelry, by 1895 their famous catalog was over 500 pages long, and featured clothes, shoes, wagons, appliances, furniture, firearms, and... musical instruments.
Muddy Waters got his start thanks to Sears: "I sold the last horse we had. Made about $15 for him, gave my grandmother $7.50. I kept $7.50 and paid about $2.50 for the guitar. It was a Stella. The people ordered them from Sears-Roebuck in Chicago."
Andy Parypa of The Sonics recalls, "We used to play in this little joint called the Red Carpet down on South Tacoma Way, and down the street, at the Tacoma Community Hall--this place'd just be jammed to the gunnels with all these young kids with their ten-dollar Sears and Roebuck guitars at what they called a 'hootenanny'" (this comes from Peter Blecha's great Sonic Boom)
The page above comes from the 1975 catalog. You could get everything you needed to get started on the guitar--instrument, case, strap, picks, and instruction book with record--for about $40, and it would be sent right to your house (this is like Amazon before Amazon).
Sears also owned a radio station in Chicago. WLS ("World's Largest Store") started broadcasting in 1924 as a service to the rural communities that Sears served. In the mornings, they'd broadcast weather and agriculture reports so the farmers knew what to expect before going out into the field. While the farmers were at work, they'd broadcast housekeeping tips for the wives that stayed back at the house. In the evenings, they'd play (live) music: the National Barn Dance was for a time the most popular radio program in the midwest, and served as inspiration for what would become the Grand Ole Opry in Nashville. Sears sold the station in 1928, but a station with the WLS call letters still exists in Chicago today.