The Midnight Cowboy in Key West


James Leo Herlihy in Key West. Photo by Bud Lee.
James Leo Herlihy in his backyard with friends, Key West, 1960s. All photos by Bud Lee. © Bud Lee / The Serge Group

James Leo Herlihy was born in Detroit in 1927 and raised there and in Chillicothe, Ohio. He lived in New York City, Los Angeles, and, off and on from 1957 to 1973, in Key West, where he became “captivated,” finding it “a wonderful place to work and write.”

“The town excited me too much,” Herlihy told Key West Literary Seminar co-founder Lynn Kaufelt. “I spent all my time exploring, walking the streets. The place was mysterious, funky, indescribably exotic. It had much of the charm of a foreign country, but you had the post office and the A&P and the phone worked, so life was easy.” Key West was still “a pretty well-kept secret,” neither a tourist favorite nor a literary and cultural hotspot: “Nightlife was delightful, totally unsophisticated, nonliterary.”

Herlihy’s work brought him celebrity in his own time. Like his close friend and mentor Tennessee Williams, Herlihy was a gay author whose works delved into taboo subjects and broke new ground for what was acceptable to major publishers. His 1958 play Blue Denim confronted teenage sexuality and abortion and was praised in a newspaper column by Eleanor Roosevelt. His novels were acclaimed by writers like William S. Burroughs, Paul Bowles, Nelson Algren, and Williams, who praised Herlihy’s writing as “luminous,” “true,” and “perfect,” hailing him as the most significant new writer since Carson McCullers. His novel Midnight Cowboy was made into a film starring Dustin Hoffman, and won an Academy Award for Best Picture despite being given an “X” rating.

James Leo Herlihy & Tennessee Williams. Photo by Bud Lee.
Herlihy (seated) with Tennessee Williams, a friend and mentor, in front of the travelers' palms at Williams's Duncan Street home.

Key West’s influence on Herlihy is plain from the settings of his fiction. In All Fall Down (1960), the adolescent protagonist Clinton Williams follows his idolized but ne’er-do-well older brother Berry-Berry all the way down to “Key Bonita,” a stand-in for Key West. His 1967 short story “A Story that Ends with a Scream” is set in Key West, as is “Ceremony for the Midget,” in which the midget is an apparition or hallucination symbolizing the spirit of a beloved bar that is closing. “The Day of the Seventh Fire” captures the mood of Key West in the 1930s. And at the end of Midnight Cowboy, Joe Buck and Ratso are riding a Greyhound to the sunny Florida of Ratso’s dreams when tragedy strikes.

One of the most exciting things about Key West for Herlihy was the presence of Tennessee Williams. He told Kaufelt, “Before Tennessee had a pool installed, he and I went swimming off the Monroe County pier nearly every summer day at twilight . . . it was inexpressibly comforting to have the daily company of a kindred spirit; just knowing we were involved in the same sort of lunatic pursuit provided some essential ground that meant everything to me.” Williams told Kaufelt of their regular ritual of meeting at County Beach, trading lines from their favorite Wallace Stevens poem, “The Idea of Order at Key West,” before diving in. As late as 1976, when Herlihy’s mother died of cancer, Williams was there for him. Herlihy wrote Paul Bowles that year that he spent three months in Key West with his dying mother: “Tennessee was in Key West during much of that time, and he was enormously considerate. Sent flowers, messages. Cooked for me. Even showed up at the funeral mass, volunteering to act as pallbearer. I was impressed and moved by it all.”

James Leo Herlihy beneath a mango tree.
Herlihy beneath a young mango tree in his backyard.

Along with Williams, Herlihy became part of a circle of friends and lovers in Key West– mostly gay writers and “theater people”– that included James “Jimmy” Kirkwood Jr., co-writer of A Chorus Line and author of cult novels and plays including There Must Be a Pony!; Evan Rhodes, the author of The Prince of Central Park; one-time singer and agent Dick Duane, to whom Herlihy dedicated two of his finest novels, All Fall Down and Midnight Cowboy; and to a lesser extent, visiting writers like Truman Capote and Gore Vidal. Author Christopher Isherwood paints the scene in an entry from his diary in August 1959: “(Broadway producer Walter) Starcke came by, en route for Japan and round the world . . . ‘Now I live by grace,’ says Starcke. ‘I live every hour of every day to its fullest.’ Actually he is in Key West, dealing in real estate and having parties with Herlihy and his friend which sometimes go on until morning. Lots of sex.”

In the late 1960s Herlihy became passionately interested in the hippie and anti-war movements. Though of an older generation, Herlihy was both a supporter and “a living participant in the counterculture,” as he told Kay Bonetti. In 1969, Herlihy purchased a cottage at 709 Bakers Lane. “My richest experience of that extraordinary phenomenon called the sixties took place in Key West,” he told Kaufelt. “The Bakers Lane cottage became a kind of ‘safe house’ for the hippies. I protected a fair number of them from the law, who wanted to drive them out of town and we had love-ins and weddings in the garden.” In a January 1969 letter to his old roommate at Black Mountain College, photographer and sailor Lyle Bonge, Herlihy writes, “I made the front pages here this week by sounding off against the police who have been arresting my friends as vagrants when they are nothing of the kind. The publicity resulted in visits from the chief of police . . . and there promises to be a new rapport or at least a stand-off from now on, or for a while, between the so-called hippy contingent and the fuzz.”

Herlihy had always been attracted to those on the fringes: “What made me so happy with those beautiful creatures was the sense they gave me that the marginal people to whom I’d been drawn all through my life were suddenly having a heyday,” he told Kaufelt. “We’ve learned since then that it wasn’t as simple as all that, but for a time, at least, the freaks really did have the establishment on the run, and nothing’s been the same since.”

By the start of the 1970s, the combination of Herlihy’s celebrity and local reputation as protector of the longhairs led to him feeling overwhelmed and desirous to leave Key West. The growing tourist industry was another factor. It was simply getting too hard to work. From California he wrote Lyle Bonge in 1973 that he was going under the name of Jamie Hathaway (a family name) in an attempt to lay low: “I’m trying not to repeat the errors of Key West where I had finally become such a public entity there wasn’t much for me to chew on.” In 1972 he purchased a farm in Hop Bottom, Pennsylvania with the idea of establishing a communal lifestyle for himself and friends like his mentor from Black Mountain, potter and author M.C. Richards. He sold his Bakers Lane home in 1973.

Although he left Key West hoping to find a situation more conducive to his writing, Herlihy would never publish another work of fiction after leaving it. He lived mostly in Los Angeles, in Hollywood and Silver Lake. He unfolded ideas in letters and worked on manuscripts including a historical novel of the Midwest and a biography of eccentric artist Henry Faulkner, but these projects never came to fruition. He acted in several plays and movies, including the 1981 Four Friends, directed by a classmate from Black Mountain, Bonnie and Clyde director Arthur Penn. Herlihy’s character in the film, a neurotic father, commits suicide in a shocking scene; sadly, more than a decade later, life would imitate art. Herlihy took his own life in October 1993.

Michael Snyder lives in Norman, Oklahoma, where he received his doctorate and teaches American literature at the University of Oklahoma. He is planning a book-length critical biography of James Leo Herlihy and is revising his dissertation on James Purdy for a book to be published by a university press.
Bud Lee was U.S. Military Photographer of the Year in 1966 and Life Magazine Photographer of the Year in 1967. More of his groundbreaking work from the 1960s-1990s can be found here and here.

34 thoughts on “JAMES LEO HERLIHY
The Midnight Cowboy in Key West

  1. mike gushee says:

    Lived and worked there from 1978 to 1994….
    sorry that the costs eventually forced me from
    the Keys up to Sebring,Fl….but they were the
    greatest years of my life,even though down there,
    ;;The times they were a changing”.
    Still miss the Key West of the good ol’days.
    Mike Gushee

  2. Beverley Kerkes says:

    My parents bought James Herlihy’s childhood Detroit home from his mother and father in 1956. I was a 12 year old budding writer (mostly intensely weepy poems about unrequited love) and inherited the bedroom that had been his. My sister got the bedroom that had been his brothers’. He wasn’t yet a famous author but I remember being quite awed a few years later when I realized who had written Blue Denim and Midnight Cowboy. His parents visited with my mom and dad quite often over the years. I guess maybe they wanted to see their old home again. The house is gone now–vandalized many years ago and finally torn down. Wish I could have met James. His parents were very nice people.

    • Joe Herlihy says:

      I was James Leo Herlihy’s nephew. He was my father’s brother. Very interesting to hear this since I have really no connection to the family anymore. Everyone has passed away from that generation.

      • Beverley Kerkes says:

        Joe, If you would like a description of the house and neighborhood let me know. I would really like to talk to you about some strange occurences that happened in that upstairs bedroom. Is your father still alive? Would sure like to ask him some questions. You can reach me at bevkerkes@yahoo.com. Hope to hear from you.

      • Michael Snyder says:

        Dear Joe,
        Thank you for posting this. I am working on a book on James Leo Herlihy. I would love to talk to you about your family sometime. I have spoken with relatives in Chillicothe, Ohio. Hoping to hear from you.
        Prof. Michael Snyder
        msnyder @ occc . edu [remove spaces]

      • Joe, I just came across this site and saw your name. As I recall, your curiosity was insatiable regarding JLH, not sure whether I coaxed your inquisitive mind into dead-ends or some degree of success. While I was profoundly straight, Jamie and I quickly became best of intellectual and social friends – we often held hands under the dinner table to ensure unanimity; I have never met anyone so similar to my mind and character than your uncle. If your curiosity remains, give me a call/email if you are ever near Newport, RI., I might fill in a couple gaps, all in respect for Jamie.

      • Cronan O Doibhlin says:

        Joe do you know if your family came from Ireland and if so when. I am an academic librarian in Cork with an interest in James. Cronan O Doibhlin

      • Tom Conten says:

        Your uncle was an incredible writer. In 1969 at age 17, I began reading Midnight Cowboy at a about 9 pm one school night. I finished at 4 or 5 am and was so devastated by the ending I couldn’t even try to go to school. My life would never be the same after that. Nothing in my entire life affected me as much as that book. I get it that some people reading it today don’t understand the hype, but that was way back in 1969 and James had taken us into uncharted waters.
        Then came the movie. I think It did a very good job of capturing the essence of the novel. I saw that film 3 times. It was X rated and won best picture. How was that possible? I don’t think it is fair that all the acknowledgement a writer gets is a closing credit, “based on the novel by James Leo Herlihy.”

      • Lynn Ray Laughlin says:

        I read All Fall Down and found it brilliant, some 40 years ago. Did you ever have a chance to meet your uncle?

      • R. W. St. John says:

        Must make you Proud to be related to such a Creative and Talented individual – I consider ‘Midnight Cowboy’ to be One of the Greatest Films of all time , although I’ve yet to read the Book !

      • James Wermuth says:

        This is my second reply to your inquiry Joe; I hope that it fills in part of your uncle’s life. I was one of three Navy Green Door interns living next door, 211 Bakers Lane, KW.
        One afternoon, I was playing my guitar and singing when Jamie knocked on the door, introduced himself, and asked if he could sit and listen. That meeting soon blossomed into a great friendship, nightly dinners, pot, acid…; Bicycle Bob, Lenore, Phoebie…, Joe Frazier (his agent) and NYC friends came and went. Occasionally, we held our version of an Esalen T session with the New Yorkers; candor was requisite.
        Jamie told me that he came from a working-class family. To earn money as a young teen, he delivered groceries for tips. During one delivery, he was raped by a gruff older fellow; it was his first sex – he never looked back. Even though he was making real money, he was never ostentatious. I only saw him lose at Tennessee Williams’ parties (iguanas and all).
        In 68-69, he used the small, walled-in unit in the back garden as his bedroom/writing studio. It was a place to get away from the group that partied in the great room, a place to talk on and on. Night rides on his scooter were one of his favorite things.
        Jamie made many close friends, he needed and loved people. One afternoon he knocked on my door and asked me to just sit with him; he told me that Tallulah Bankhead had died and how she helped him fit in with Hollywood society. He must have cried for an hour.
        Just before leaving KW, Jamie was my best man – oh there has never been such a civil ceremony with Lenore officiating and Jamie putting on such gracious theatrics. It was a lovely hoot, a last hurrah before driving up to Groton, CT.
        I hope that this helps to fill in a bit about James Leo Herlihy.

  3. Mary Ann Howard says:

    Thank you for the wonderful article & photos. I came across Mr. Herlihy’s writings after reading that William Inge’s screenplay was based on a James Leo Herlihy novel (All Fall Down). Of course, from there I had to find everything he’d ever written and devour it. I can’t wait to read the biography. And I feel lucky to have landed here and see posts from a former inhabitant of his childhood bedroom and from his nephew.

  4. I have several letters from Mr. Herlihy from 1987.. I wrote to him thru his agent and he hand wrote me letters back. I still have them. I asked him all kinds of questions about ” Midnight Cowboy” both the novel and the movie.He was kind enough to take the time to write me and I was very impressed with that.

    • Michael Snyder says:

      Hi Rick, I would love to read those letters. Is there any chance you would be willing to make photocopies of them for me?
      Michael Snyder
      mkesnyder AT yahoo.com

  5. William Rothlein says:

    I got to know Jamie or James Leo Herlihy as he was known in the mid seventies in Los Angelos. He was a good friend of My friend James Kennedy who passed away one year ago this month. At that time we were working at the Actors Studio in Hollywood. A truly beautiful man, we spent some time together talking about life and the work in film and theatre. Last night watched Midnight Cowboy for the first time since it was released. Tremendous film. It brought back many memories. William Rothlein

  6. Larry Claypool says:

    I remember Baker Lane very well-even lived there in one of the guesthouses separate from the main house for a few months. We definitely had some great times there-(though I was not gay myself whereas most people hanging at jamie’s were) – I still found acceptance and enjoyed many a good acid trip and many lievly a conversation there.

    • Lloyd(Lou)Cox says:

      I met Jamie when I returned from overseas, in November 1968. I was stationed at the Naval Base, on the USS Calcaterra. I brought back some Marijuana and met some hippies to share it with and they took me over to Jamie’s house and we smoked, tripped and had great conversations there. Listening to the music of that generation was also beautiful and new. Met many of his friends, who were from all parts of the country, from east to west, north to south. Everyone was wonderful and left a lasting impression of love and acceptance and was the footnote to my personal journey into the hippie era , after my discharged from the military. I will always remember Jamie and friends and 709 Bakers Lane!

      • lou,

        like you I was stationed on the Calcaterra (DER 390) in 1969 and we may have known each other.

        I was GMG3.

        also met Jaimie not knowing who he was but remember his as a kind and gentle soul…

        • Lloyd Cox says:

          Hi Bill
          I was discharged in April of 69. was on the Calcaterra since 1967. I had just come back from Operation Deep Freeze, in the Antarctic in November of 68 when I met Jamie and friends.
          Where you there for that? I had studied Sonar at the Fleet Sonar School, but got into a fight and kicked out on Graduation Day and ended up being stationed on that ship as a seaman deck aid.
          Did you know Michael Page, Trick Willy or Tony Braxton? Where you on the ship when we were in New Zealand?
          If so, please give me a call or text or email, at 303-358-6342, cox290@msn.com
          ph# is from Denver, but I live in Berkeley, CA and I’m originally from Cleveland, OH
          hope to hear from you

      • Scott Glenn says:

        Were you at the party at Jamie’s house when we all got to listen to the Beatles White album , which one of Jamie’s disc jocy friend brought down from NYc the night before it’s first air play on radio ?
        Please let me know.

    • Hi Larry- Did you know my parents, Jim and Ann McLendon, who lived next door at 711 Bakers Lane in the early 70’s? I was a toddler then, Jamie’s cat used to sleep in my crib evidently. Could you contact me if so? FInd me by googling Stacey Craft Basalt CO

  7. sara ryland says:

    I lived in KW as a child, Mr. Herlihy’s parents , Bill and Grace lived behind us. We visited them often and sat in,their backyard garden. We gave them momentis of grade school and had biscotti for the first time with them. I never knew of James at the time, but we loved them like grandparents as ours lived out of town. Great memories of two very loving people.

    • Joe Herlihy says:

      Too wild, Sara! To read someone’s comments about my grandparents is really something. Sadly, my grandfather (Bill) passed before I was born in 1969, and my grandmother (Grace) passed when I was only two, in 1976. I don’t remember her. I wish I would’ve had the chance to know them both. At least for enough time to have a few memories.

  8. Hello,

    I’m producing an independent documentary about an underground gay and artist culture in Lexington, KY since the Civil War and some of the characters dead and alive, include Henry Faulkner (painter), Tennessee Williams, Robert Morgan among others. Henry, TW and Jamie Herlihy are part of the stories that are told having impacted a younger generation of gender bending, sexual outlaws, camp, and drag queens.

    I’m looking for images of Key West of the 60s, and anything that might include Henry Faulkner, Williams and Herlihy, houses that may have housed any of them.

    I would be happy to share what I have including oral history.

    Jean Donohue
    The Last Gospel of the Pagan Babies

  9. Marsa Hightower says:

    I remember well Jamie’s backyard and swinging to the sounds of Donovan. I came to Key West with Walter Starcke, and lived with him on Pearl Street until a dispute landed me on Tennessee’s couch for a brief spell. Watching Space Odyssey 2001 and Yellow Submarine at the theater on Duval with Walter and Jamie. Head Beach and evenings at Capt Tonys. It was a special time.

    • Lloyd(Lou)Cox says:

      I met Jamie when I returned from overseas, in November 1968. I was stationed at the Naval Base, on the USS Calcaterra. I brought back some Marijuana and met some hippies to share it with and they took me over to Jamie’s house and we smoked, tripped and had great conversations there. Listening to the music of that generation was also beautiful and new. Met many of his friends, who were from all parts of the country, from east to west, north to south. Everyone was wonderful and left a lasting impression of love and acceptance and was the footnote to my personal journey into the hippie era , after my discharged from the military. I will always remember Jamie and friends and 709 Bakers Lane!

  10. Hey,

    I live in 709 Bakers Lane now and have definately seen Herlihy’s ghost a few times! I love this article. If you are in Key West and want to see the property, let me know. The peep hole is still there

    Thank You,
    Brian Antoni


  11. I am co-authoring the sequel book on the history of Silver Lake (the first one is entitled “Silver Lake Chronicles: Exploring an Urban Oasis in Los Angeles”). The 2nd book will focus on the Iconoclasts, Bohemians &Visionaries of the Modern Era and will include a story on James Herlihy. We are hoping to find photos of Jamie in connection with his life in Silver Lake. Especially helpful would be a photo of the Silver Lake house or photos of him hanging out there or in the community. If you could give us a lead on this it would be quite valuable. We have photos of the house now but it has been drastically altered since Jamie’s time there.

    Thanks for your consideration. Michael Locke, Author and Editor

  12. Larry Claypool says:

    very cool Brian- I remember the peephole very well -we could always check who was at the gate before opening it up. I lived in one of the guesthouses but like everyone partied in the main house. Is the pillar still in there. we used to have this pillar you could climb up on that had a mattress up top. It was surrounded by high quality stereo speakers and you could lay tripping on acid for hours diggin the stores through an open skylight and listening to music

    • Sally Reno says:

      I lived at 709 Baker Lane mid/late 1970s. When I moved out (78?) Kirby C. basically gutted the interior to make it more marketable as a rental so most of what came before indoors is that long gone. I Think I know what Brian is talking about with the “pillar”….there was a low half-loft and definitely a skylight. Also the peephole in the gate. However, in my day most folks ignored the gate and either just climbed over the wall or went down the other side of the house (unfenced) It was kind of maddening. I lived there alone most of the time but people just came pouring in at all hours. I installed a wrought iron fence on that side. Still there? I’m puzzled by Larry’s reference to guest houses. Where? There was a tiny shed, always flooded, against the center of the back fence. Really tiny, no windows, dirt floor, hardly a guesthouse. I can see from the lead photo above that the fence was in the same place in Herlihy’s day and the corner of the yard shown was the same. The other side had a funky fish pond. No room for guesthouses anywhere else. In my day, Henry Faulkner still rode around town and down the lane on his bicycle, in his mother’s wedding dress, singing blues songs (great voice actually) every full moon. Lots of ghosts (and a few ghouls) in my day but none were Herlihy’s then as he was still alive.

  13. My Grandfather was Bill Herlihy – Jamie’s older brother. I don’t know about the family much because my Grandfather distanced himself. My mother was an only child and I have only heard strange and difficult stories about the Herlihy family. My Grandfather passed some years ago. I was told that All Fall Down was rumored to be based on my Grandfather which caused some issues in the family. My Grandmother did have a car accident when she was pregnant with my mother – her breaks went out – and I was told that story many times by my family. I was told that the Herlihy children had a difficult childhood. It is interesting and nice to read these kind comments about Jamie and his parents – my Great Grandparents. I never knew him or the rest of the family.

    • So many good stories..unsure where to type in my brief experience with Jamie.I was at Temple University in Philadelphia ,having just gotten out of the Army in’70 and took a road trip in one of those Drive-a-way cars with a friend during Summer break..I think it was 1972..He was hitchiking near Miami and we picked him up..said he was headed to Key West..We had to deliver this car somewhere below Homestead and there was still some devastating damage from hurricane Andrew..I asked what he did in Key West and as I had never actually been there..He told us he was a writer and my friend who was majoring in English..started grilling him about what did he study in college,what courses he took..kind of embarrassed me..Jamie responded,he’d studied Sculpture & Theater..I think mybfriend was miffed he wasn’t an English Major..I asked if he’d gotten anything published and he responded “Well you probably never heard of it..Season of the Witch.”We hadn’t and then he said you probably heard of my other one, Midnight Cowboy.I almost ran off the road.I was at a loss for words. We had both seen the movie. I saw it at the Army Theater .He said he enjoyed college, but got his ideas from his life experiences..I would have driven him all the way to Key West, but we had to deliver the car to its owner, so we parted company after about an hour..In hindsight I should’ve have just taken him to Key West and delivered the car a day or two late..but it wasn’t to be..I never got to see him again and was saddened when I heard of his death by suicide in ’93..A very tragic end to an incredible person..whose company I only got to enjoy for an hour or so.. Barrie D.Hazzard, Kennett Square,PA.

  14. Used to bomb around times square when we were kids in the late 60s.Anything for a goof.It was just like in the movie.Youd be at Fabers or playland playing Sink the Jap battleship or something and some old queen would come sidling up to you-saying Hey kid you play that game really good! ya wanna go for a hot dog and soda?My treat.Some of them made your skin crawl.Their depravity was written all over their face.I think the movie was better than the book.Woinder what mr. Herlihy thought off that?
    Oh yeah,my fave was Top Gun or Get the drop on the western outlaw.just like in the pic of Herlihy goofin in t. sqware.The outlaw won most of the time.That game cost 25cents then. A tad pricey

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes:

<a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>