The original Ray's Bar & Grill was opened in December 1992 by Ray Jacobson. In Step's 'Steppin Out' column mentioned it as a "comfortable, cozy bar and grill". An advertisement says: "Madison's finest gay owned & operated Bar & Grill, A Place for Clean, Healthy Fun". Thus begins a long winding road and a string of relocations and renamings.

As the bar's second anniversary approached in October 1994, an article appeared wherein it was announced that owner Ray was opening a second location at 3052-3054 W. Washington (the old 'Club 3054'), which he planned to call 'Reflections'. At the second anniversary celebration, Ray was referred to as "owner of Ray's and now Geraldine's". Ray had decided to name the new bar "Geraldine's" after his mother, rather than the planned name "Reflections".

But by January 1995, the original Ray's bar at 2415 Winnebago Street was closed. A mention in the column 'Steppin Out' said that "owner Ray, who recently bought, remodeled and opened Geraldine's up the street at 3052 E. Washington Avenue, sold Ray's back to the original owner". So for some reason Ray had decided to make the new bar his only bar!

Things are murky for Ray's loyal customers for several months. For a time it seemed that Geraldine's was a 'western' bar, advertising Western Line Dancing with 'Dairyland Cowboys and Cowgirls', and at least one live country-western singer. It's not until August 1995 that an advertisement for Geraldine's announces "Ray's Bar is BACK & Open Friday, September 1/ Alongside Geraldine's (Entrance on east side of building) We have set aside a new space designed for men in mind."

So Ray's Bar was back, but as an afterthought and side addition to the newer Geraldine's space. Then in February 1996 another Geraldine's advertisement includes a box reading "Watch for the opening of Ray's Restaurant- coming soon inside Geraldine's."

In November 1996, an advertisement headed "Geraldine's / The Men's Room & Ray's Cafe" is promoted as "4 Year Anniversary!!". The ad goes on, "We've changed buildings, added new names and spaces, but Ray's business is now 4 years old and still growing." The ad mentions a "Men's Room Grand Opening" upstairs.

By July 1997, Geraldine's is being advertised as a complete entertainment complex, with 4 bars, dancing, restaurant, outdoor patio with volleyball, Geraldine's Restaurant & Bar, The Men's Room levi/ leather bar on second floor, Ray's Bar and Phoenix Patio Bar. It's unclear to patrons whether "Ray's" is still a separate entity at all or now simply a segment of a new Geraldine's identity.

Things finally clear up when a 5th Anniversary advertisement reveals that as of January 1, 1998, "Geraldine's will be going back to our roots and our original name" as "Ray's Bar & Grill". For the next couple of years it appears that the bar was fairly successful, although it no longer seemed to be doing any advertising as we have not located many examples.

Then in late 2002 the bar disappears from Bar Listings in media. One of the last listings was in the October issue of Quest magazine (and considering that listings were usually updated infrequently, we can speculate the bar may have closed a month or two prior).

Was this to be the end of Ray's Bar? It appears to have been closed and out of business from mid-late 2002, for about a year.

The bar pops up again in Bar listings in mid-2003, along with a photo appearing in OutBound magazine's July 2003 issue mentioning a "New Ray's". Because of the lack of advertising or even mentions in LGBT periodicals of the time, we don't know what happened in the prior year that caused the closure of the old Geraldine's location and eventual move. A passing reference is made in the OutBound column 'Tales from the Trailer' by Terry Halverson in the September 2003 issue of OutBound magazine which reads: "Ray's closed his location at 3054 East Washington and moved to a new location at 2415 East Washington Ave next to Red Letter News."

Mid-2004, the advertising budget must have been pumped up, as some flashy ads began to appear. A year later, a few small ads and Bar Listings began to reference a "Jake's (inside Ray's)". Who is Jake, and why the separate bar space (and space name) within Ray's bar?

Then in October 2005, a large ad appeared, sporting both the Ray's and Jake's logos, with the Jake's logo noticeably larger. The ad reads: "Ray's Bar has another new addition- THE WAREHOUSE", opening for Halloween. The ad goes on to say: "This party will be reminiscent of the Old Hotel Days" (referring to the long-gone Hotel Washington complex).

We have found no advertising or references for the next 18 months.

Unfortunately, the bar was to come to a sudden and undignified end. On April 9, 2007, the bar was closed and owner Ray Jacobson revealed was being evicted. Apparently rent checks had recently been given to the landlord with unsufficient funds in his account to cover them. After about 14 years of off-and-on business in three different locations, Ray's Bar was no more.