Heartbreak Hilarity: ‘The Heartbreak Henry’ comes to the Claude Gentry Theatre

Baldwyn set to stage story of David Sheffield – former SNL writer, man behind Eddie Murphy’s comedy – and his time running a small hotel in 1960s Oxford, Mississippi

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BALDWYN | Off The Square in Oxford a long time ago there was a hotel, the Henry Hotel. It wasn’t a large hotel, only holding around 20 rooms. What those rooms held, though, was comedic gold – and one of America’s greatest comedic talents just happened to run the place during his freshman year of college.

Christy McBrayer, left, is directing “The Heartbreak Henry,” August 11-13 in Baldwyn. The play was written by comedic legend David Sheffield, right, former Saturday Night Live head writer and the chief comedy writer for actor Eddie Murphy. News photo/Jason Collum

The year David Sheffield was put in charge of the Henry Hotel in Oxford in the mid 1960s is the basis for the play, “The Hearbreak Henry,” which will be performed in Baldwyn August 11-13 at the Claude Gentry Theatre. Directed by Christy McBrayer, “The Heartbreak Henry” features a cast of 17 playing a wide variety of characters – from a pair of redneck house painters in residence to a mother-daughter hooker duo – characters Sheffield met in a decrepit hotel that rented rooms for $3.50 per night, or $4 if you wanted a private bathroom.

“There were a few people who lived there full-time, mostly students,” Sheffield said. “Then there were some transients. We got a lot of hucksters and drifters.”

Sheffield happened upon the job his freshman year at Ole Miss. He didn’t like living on campus and could not get along with his dorm mate, so Sheffield looked to live off campus. That search took him to The Henry. The owner paid Sheffield $100 a month to essentially run the place and be there at all times except for when he was in class.

“I had to be there in case some drunk stumbled in and wanted to rent a $3.50 room,” Sheffield said.

This led to many an interesting encounter, including when Sheffield found himself being arrested by Oxford Police one night for solicitation – because of the “women of the evening” who were there. The police relented but told him he had to evict the ladies. That led to an interesting conversation between him and the mother-daughter duo, whose services commanded $8 and $10, respectively.

Another character who is featured in the play was an older lady whose drink of choice was witch hazel. Yes, witch hazel.

Career in comedy

Sheffield had already been writing comedy when he went to work at The Henry. Despite the fact he found himself in some difficult situations at the time, he still saw the humor in his situation and surroundings even then.

Sheffield left Ole Miss after his freshman year and transferred to the University of Southern Mississippi, where he met a friend, Patrick Weathers, who ultimately became a connection between McBrayer and Sheffield and his wife, Cynthia.

After the Sheffields had moved to Ocean Springs where Cynthia had taken a teaching job, Weathers contacted Sheffield and told him to send him some comedy sketches to present to the producers of Saturday Night Live as Weathers was auditioning for a role. Sheffield did and the producers liked what they saw. After five or six weeks the producers had been so impressed with Sheffield’s submissions that he was offered a job – a 13-week contract. So Sheffield moved his family to New York on the belief that he would make it. 

This was at a time when SNL was in significant retooling and the previous cast was having to be replaced. It was at this time that a 19-year-old fresh face, Eddie Murphy, was brought on as a featured actor, and Sheffield met writing partner, Barry Blaustein. The two went on to become Murphy’s chief writers for his sketches. That also began a more than 40-year working relationship between Sheffield and Blaustein that has produced some of the greatest comedy sketches and movies of the past two generations.

As it turned out the move for Sheffield was a safe bet.

“In the third year, I was made the head writer and supervising producer of Saturday Night Live,” Sheffield said.

The success continued after Murphy’s career ballooned beyond Saturday Night Live, with Sheffield writing many of Murphy’s hit movies, including “Coming to America,” “The Nutty Professor,” and “Boomerang.” Sheffield also wrote the sequel, “Coming 2 America,” which is available for viewing now on Amazon.

McBrayer came to know the Sheffields while she was living and acting in Hollywood. She was acting in a small play on Santa Monica Boulevard that the Sheffields attended along with Weathers, who McBrayer soon thereafter began dating and then got to know the Sheffields. Having known the couple for so long she now feels an extra burden to give the best possible performances of Sheffield’s play. This will be the fourth city to host the play (behind Biloxi, Oxford, and Slidell, La.) – and she wants it to be the best.

“I’ve been leaning big time on Dave, and I want to really do his baby justice,” McBrayer said. 

With such an extensive and varied cast – Sheffield said he found it difficult to cut out some characters from the play, which he finished in 2018 – McBrayer had to cast her net far and wide and has secured several seasoned actors for some roles. She’s also filling one of the roles herself. Bringing such a large cast to play on a small stage has its challenges, but McBrayer is pleased with how practices have gone.

“It is quite the undertaking, but so far I think we’re in really good shape, and it’s a lot of fun,” McBrayer said.

McBrayer has had to make some adjustments, but she has been keeping Sheffield abreast of changes she’s needed to make.

“I am putting some twists to what David wrote due to (casting) limitations,” McBrayer said. “Sometimes I have turned a couple of characters that are male into female and vice versa that have given a little bit of a twist to it.”

The play is being produced by McBrayer’s Southern Fried Chickie Productions and Six Shooter Studios. McBrayer said presenting “The Heartbreak Henry” – which is the first play to be hosted by The Claude Gentry Theatre since Covid wrecked everything in 2020 – is in keeping with a philosophy shared between her and Six Shooters’ Clark Richey and Amye Gousset. That shared idea is that while many mainstay and classic plays are worthy of being presented and are crowd pleasers, the three also want to present new and innovative material and shows to area audiences. “The Heartbreak Henry” fits that bill completely.

Performances are set for 7:30 p.m. August 11-13.  Tickets are $22 for reserved seating and can be purchased on Eventbrite.com (click this link to go there). Scroll down the page to select the performance you want to see and reserve your tickets today.

For more information, see updates on The Claude Gentry Theatre’s Facebook page.

Six Shooter Studios’ Clark Richey, left, and Southern Fried Chickie Productions’ Christy McBrayer, who is directing David Sheffield’s play, “The Heartbreak Henry,” laugh as Henry shares a story during a visit on the stage of the Claude Gentry Theatre in Baldwyn on Saturday, July 16, 2022. News photo/Jason Collum