The first gay bar in this space was apparently the "Anchor Inn", but almost nothing is known about that bar.

The Riviera Cocktail Lounge and Restaurant opened on November 25, 1949. An ad in the December 21, 1949 Milwaukee Journal Sentinel of course didn't reference it as a "gay bar", but called it "A new and different place for your wining and dining pleasure". The ad then mentions "Chef 'Eli' and Waiter 'Leonard'", and states "A famous chef and a noted bartender join their talents"; those may have been names familiar to gay men of the time.

Researcher Michail Takach discovered on NewsBank in Feb-2020 that "The New Riviera (401 N. Plankinton Avenue) was opened by John Balestrieri and cousin John Triliegi as a cocktail lounge on November 25, 1949, almost 20 years before Stonewall. It was taken over by Tony Machi sometime in September 1951 and became "Tony's Riviera Cocktail Lounge" (although still commonly called simply 'The Riviera'), offering 35 cent Martinis. Until it burnt down 13 years later (see below), Tony's was one of the hottest gay bars (and hustler joints) in town."

Takach also added info about a possible gay bar across the street: "On July 22 1960, the Milwaukee Police Department voted against giving Mary Wathen a license to operate the Sunflower Inn (1806 W St Paul Ave.,) when “Dirty Helen” Cromwell retired due to financial difficulties. Wathen had reluctantly managed "Mary's," one of the city's first gay-for-pay bars at 400 N Plankinton Ave, from 1959-1960. Police Chief Johnson advised against licensing as Mary’s had attracted “undesirable elements - even more undesirable than Dirty Helen herself.”

Another article from a 1961 Milwaukee Journal Sentinel issue demonstrates one method of harassment toward gay bars at the time. Notoriously homophobic judge Christ Seraphim fined one of the owners, Andrew Macki, $50 for permitting dancing. The defense contention that the ordinance was not violated because the three sets of dancers were men was rejected by the judge, who said "This place caters to that kind of clientele". It's interesting to see how widely the Riviera was known as a gay bar, so long before Stonewall.

The Riviera is largely remembered now for a huge fire that claimed the bar and the entire building.

A podcast about the Riviera and the fire was recorded by historian Gavin Schmitt. (Much of the information from the podcast comes from this website and the Takach book "LGBT Milwaukee".)

According to rumor, in March of 1964, there was a lover's spat; one of the two men went around the back of the building (a 4-floor brick warehouse), and set the building on fire (a grain elevator). The contributor who relates this story remembers that when the front wall of the building collapsed, it crushed the fire department's ladder truck.

Historian/ researcher Michail Takach makes sense of the rumors in his book, "LGBT Milwaukee":

The Anchor Inn (401 North Plankinton Avenue), located in the historic Hunkel Seed building, was already an unofficial gay meeting place by the 1950s. In 1952, the 3,000-square-foot tavern was leased to Peter Machi of the Old Third Ward family, who opened Tony’s Riviera Cocktail Lounge. Tony’s Riviera became quietly known as the premier gay bar of the 1950s. The Machi brothers invested considerable money—and involved many sponsors—while carving a modern lounge out of the historic grain mill. “On Sunday afternoons, the place was loaded with cops,” said one contributor. “Sometimes, they’d bring their women, but rarely did they bring their wives.” Patrons remember policemen visiting the Riveria’s basement, which allegedly housed an illegal booking joint, and stuffing envelopes into their coat pockets on the way out. Milwaukee police suspected the Riviera of paying “insurance,” but the Machi brothers denied being shaken down by any syndicate.

On March 14, 1964, a catastrophic five-alarm fire consumed the Riviera and devastated the block. “I was on vacation in California,” said a contributor, “when someone called me to say ‘your house is on fire—come home!’” At 6:00 p.m., someone ran into the bar and yelled “Fire!” Bartender Richard Isensee remained open until policemen ordered him to evacuate. “When we left, the ceiling was on fire,” said Isensee. “But you just don’t leave a dirty bar.” The ruins smoldered for a week. Although arson was suspected, FBI documents note that the underinsured tavern was a “profitable fag joint.” Rumor has it that a lovers’ spat ended with one of the men setting fire to the building. The Riviera relocated to 952 North Plankinton Avenue until its 1967 demolition. Later, the Machi brothers opened Teddy’s (1434 North Farwell Avenue), a disco and live music venue that is now Shank Hall.

(The book "Beertown Blazes, A Century of Milwaukee Fire Fighting" by R.L. Nailen and James S. Haight (Renaissance Books), recalls what is likely that fire on page 240, as one of the Top 100 fires in the city. It documents the fire as follows: "March 15, 1964 Northern Floor Covering et al; 401-411 N. Plankinton; 4 (story) brick 100x125 mercantile & storage. Box alarm 6:18pm for fire in rear loading dock; ceiling flashed over while lines being laid; hot air explosion involved 2nd floor; 5 alarms by 7:30. Four men of Truck 3 trapped on 3rd floor, rescued via aerial ladder. Fire out all floors and through roof; 4 special calls; north wall fell 8 p.m. crushing Truck 7's trailer. Under control 3 a.m.; ruins smoldered for a week. Response 160 men, 18 engines, 6 trucks, fireboat; 36 hose lines; 10 million gallons water. Loss $185,370.")

(The book, "LGBT Milwaukee" by Michail Takach, seeks to make the story of LGBT Milwaukee accessible, visible, and portable for future generations--before it is too late. The Riviera is one of many early LGBT landmarks documented in the book.)

More information about this business is welcomed from anyone who can contribute it.

Recollections: The following are recollections of others who have been kind enough to submit their personal memories to the webmaster. You are welcome to do the same!

Opening advertisement, Nov. 25, 1949 (Milw Journal Sentinel)	Advertisement, Dec. 21, 1949 (Milw Journal Sentinel)	Tavern fined for dancing violation, 1961 (Milw Journal Sentinel)

Listings in early "Gay Guides": (For more information on the Guides, click here.)

1963, Lavendar Baedeker   History of the Baedeker Guides   Index Listed as "Riviera"	1964, "Directory 43"   Title Page   Introduction Listed as "The Riviera (Tony's)"	1964 Guild Guide   Title pg   Editors note   Note concl Listed as "Riviera Cocktail Lounge"
1965 International Guild Guide   Title pg   Editor's note   Codes Listed as "The Riviera" at 952 N. 3rd St.	1966 Bob Damron's Address Book     Publisher note Listed as "New Riviera" at 3rd & Plankinton	1966 Lavender Baedeker Guide     Back page Listed as "The Riveria" at 952 N. 3rd
1966 Male World Guide     Index, excerpt Listed as "Riveria" at "401 N. Plankinton (or 952 North 3rd St.)"