The Trials And Tribulation Of “Miss Judy Garland” (AKA Timmy Riley)-With The Marilyn Monroe, Tony Curtis, Jack Lemmon Film Billy Wilder’s “Some Like It Hot” In Mind    

By Bart Webber

Timmy Riley, the youngest brother of the legendary high school and college football player Thunder Riley who led North Adamsville High School to the state division championship his senior year (1961), and also a fairly good football player, a tackle, in his own right a bunch of years ago told me that when he saw very masculine male star actor Tony Curtis and less masculine (maybe gay he thought at the time based more on his pretty face than any facts he knew then) star actor Jack Lemmon cross-dressing in the classic Billy Wilder film Some Like It Hot he began to feel free, discreetly free, to do the same. To go to his mother or one of three sisters’ closets and try some silky items on. As far as Marilyn Monroe who would become a darling of the cross-dresser and transvestite (now transsexual or some such term) sets (they are different) and behind number one queen Judy Garland would be the most popular character on the drag queen circuit left him cold. Nada.         

Now today that whole scene might seem archaic, seem old school and old-fashioned but let me tell you that was not the case back in the day. During the early 1960s one Timmy Riley, whatever his very secret identity, was a charter member of the Tonio Pizza Parlor corner boys from the Acre, read working poor, section of North Adamsville. Said corner boys I am ashamed to admit today thought nothing of “fag”- baiting each other, always testing for signs of anything less than whatever passed for the rules of manly behavior in those sullen days (and mostly poor boys long way from “home” weekend nights).

Moreover, we would fag-bait others who showed any sign of the feminine. Would and am very ashamed on this one go down to Provincetown, usually, no, always drunk looking to fag-bait, and beat up the real gays we knew populated that town. And the leader of the pack at who knows at what emotional expense, the secret cross-dresser and closet gay guy of his mother and sister’s silky goods was one Timmy Riley corner boy in good standing, Tonio’s Pizza Parlor. That would not always be the case since after high school maybe a little later, I had lost contact with him for a while when I was away at college and in the military in the late 1960s, when being openly gay was starting to be somewhat accepted he made the cardinal mistake of telling his pious Roman Catholic parents and a few others of his real sexual identity. You could not do that that then in the Acre and certainly not to pious parents. The heat got so bad, the backlash so rough he had to flee town and would eventually wind up in gay-friendly San Francisco. (His parents never were reconciled with Timmy’s decisions, especially to go to Frisco and become a leader in the drag queen community, not exactly the same as the gay community, but definitely not Roman Catholic-stamped and all parties remained estranged until his parent’s deaths.)

Like I said I lost contact with Timmy for a while until I ran into Allan Jackson, another corner boy, at a class reunion who told me that he had been in contact with Timmy for a while. More than that really Timmy in Frisco did what he always wanted to do to express himself ever since that long ago film film exploded in his face. He would go to work in a “drag queen” circuit club in North Beach as Miss Judy Garland complete with songbook. Eventually and this is where Allan comes in big time Timmy would manage then buy with Allan’s financial help the then notorious but now merely world tourist attraction KitKat Club in North Beach. And the number two fag-baiter back in the day behind one Timmy Riley-yes- one Allan Jackson. Go figure.

I would eventually get out to Frisco and see Timmy, oops, Miss Judy Garland, and cut up old torches. That is when he told me about the Tony Curtis and Jack Lemon fantasies that drove him crazy all through high school. I cried, or maybe we cried a tear at the time for old times’ sake. Recently on another trip out to Frisco I stayed at one of Timmy’s (you know who I mean) condos and one night he came over after work and asked if I would like to see Some Like It Hot which I had either never seen or had seen only parts of. I said sure. I had to laugh along with Timmy as he gave a total critique of what was wrong with the cross-dresser pair from their dippy hats to their silly shoes. Had to laugh as Timmy gave an equally powerful critique of the basic premise of the film that cross-dressing and such was okay as long as you returned to real manhood when the coast was clear. Meaning once the bad guys who caused the need for feminine disguise were wasted and everybody could revert to homogeneity. Except guys, gay guys like Timmy, like Miss Judy Garland had to suppress their harmless desires at who knows what costs. Amen.