Around 1900, The Crazy Horse edifice was built as a hotel, which supported the local train station that was across the way. As time progressed, this area of Bloomington became known as the levee, and it was considered the rough side of town. Rumor has it that the upstairs to this building, which now houses the offices of The Crazy Horse, used to be a brothel.
In 1979, new ownership took over and renamed the establishment the Gentry Remedy Co. The name corresponded to Gentry Street, which runs perpendicular to Kirkwood, behind what is now the Hyatt hotel. There are still signs of the Gentry Remedy Co. as you look at the etched glass above the patio doors.
In 1982, the bar was remodeled, and once again, it was renamed. The Crazy Horse was first identified as a meat market, and it was a dance bar and student hangout. In 1985, new ownership changed the business to a biker bar/jazz bar, but it remained open for less than a year.
Two Rats, Inc. purchased The Crazy Horse in April 1987, and they still own it today. The Crazy Horse is one of three businesses owned by the company, along with the Upstairs Pub on Kirkwood and The Alley Bar, which is one block east of The Crazy Horse.