Paul Simon may have put more effort into The Capeman than any other project in his long career. He certainly put in more time. Unfortunately, Simon’s attempt to conquer Broadway led to his greatest failure.

Even though the singer-songwriter expressed admiration for the show tunes of yore (and songwriters such as Cole Porter and George and Ira Gershwin), he admitted to being turned off by the musical theater of the ’70s and ’80s – the same era in which Simon was scoring hit after pop hit as a solo artist. It’s not just that he wasn’t the biggest fan of Andrew Lloyd Webber, he felt that most of the music was bland.

“There are all of these different stories out there, but the music kind of all sounds the same,” Simon told the Baltimore Sun in 1997, also expressing his dislike for how the musical component appeared secondary to the lyrics. “I think that’s deeply unmusical.”

And so, after Simon came up with the idea to make his own production, he planned to come up with the melodies, rhythms and songs first. Although he didn’t begin earnest work on the show until 1993, the initial spark had happened in the late ’80s while Simon was working on Latin music-inspired The Rhythm of the Saints.

Somewhere along the way, the Latin rhythms with which Simon was playing reminded him of an incident that occurred in New York City in 1959, when he was a teenager. A 16-year-old Puerto Rican gang member named Salvador Agron killed two other young men when he mistook them for members of a rival gang. He was nicknamed “the Capeman” for the red-and-black cape he wore when he committed the murders. Agron was convicted and sent to prison, later rehabilitated himself by getting an education, becoming a writer and speaking against violence before he died in 1986.

Simon found poetry in the arc of Agron’s life and began to create music to suit the story: traditional pop, as well as sounds based in Puerto Rican plena and bomba rhythms and doo-wop styles to evoke the '50s. The Capeman was an ambitious project, but the artist was coming off of two albums (Rhythm of the Saints and Graceland) in which he had merged musical styles from around the world and been rewarded with acclaim and multi-platinum sales.

Listen to Paul Simon Perform 'Adios Hermanos'

Simon seemed sensitive to the fact that he was an outsider to the tale – a middle-aged white guy telling a Puerto Rican man’s story – so he invited Nobel Prize-winning writer and poet Derek Walcott to aid with the lyrics. Walcott, like the real-life protagonist of The Capeman, was also born on a Caribbean island (although he was from St. Lucia, not Puerto Rico). After Simon created the musical templates, he and Walcott collaborated on the words.

“The first and most important test of that was: Would the Puerto Rican community believe it?” Simon said. “Because if it didn’t pass that test, then it probably wasn’t telling the story in a really compelling way.”

Over the course of multiple years, the duo created and Simon eventually recorded the songs. Then he began to assemble a crew and cast to bring The Capeman to life. As they worked, Simon and Walcott sometimes earned the desired reaction from the project’s Latino musicians and performers (including Marc Anthony, Puerto Rican by heritage, and Ruben Blades, from Panama). And sometimes, they learned that the words didn’t appear authentic. That was just one of the reasons The Capeman had its premiere date pushed back while the production underwent major rewriting in December 1997 and January 1998.

But before The Capeman even began preview performances at New York’s Marquis Theatre, Simon released his own sort of preview of the musical. Released on Nov. 18, 1997, Songs From the Capeman featured a selection of tunes from the musical often sung by the songwriter (who was not a cast member), becoming the artist’s ninth solo album. Just as Simon had made the unorthodox move of writing music for the show before the lyrics, he put out a semi-soundtrack album before audiences had seen the production.

If Simon and the production’s producers expected Songs From the Capeman to stir additional interest in the upcoming Broadway spectacle, their hopes were dashed when the album became Simon’s first album not to enter the Top 40 on Billboard’s album chart (it stalled at No. 42). Fan and critical reaction was mixed.

Some Simon devotees were confused by the profanity in the lyrics – which might have been appropriate coming out of the mouth of a violent teenage character, but sounded awkward when Simon sang them. Plus, with material so tied to a story and vocal contributions from Anthony and Blades, this wasn’t quite a real solo album. On the other hand, with a three-hour production distilled into 55 minutes and many tunes sung by Simon, Songs From the Capeman was hardly a typical Broadway cast recording either.

Actually, the original Broadway cast of The Capeman never saw their recording of the musical hit stores. The production just didn’t last long enough. After officially opening on Jan. 29, 1998, the show met harsh criticism and could not be sustained for long as a commercial venture, closing after only 68 performances. The Capeman lost an estimated $11 million.

Broadway traditionalists were vindicated while Simon was handed a rare failure in a run that had included so much success in pop music. Although he was disappointed by The Capeman’s short run, he expressed gratitude for the creative experience that it provided. He later spoke about how difficult the process was for him.

Watch Paul Simon Talk About 'The Capeman'

“It’s not that easy to write for the theater for the first time,” Simon told USA Today in 2011. “You really need a guide. For people coming out of popular music, writing songs that further the plot is different from writing whatever is on your mind. It’s a different discipline.”

Even though The Capeman is regarded as one of the more famous flops in modern Broadway history, the production is not without its supporters – especially when it comes to the music. More than a decade after the show concluded its short run, the tunes were presented in other New York productions that were closer to a concert than a lavish stage spectacle.

Simon has attempted to rescue some of the Songs From the Capeman too – performing a range of selections with a doo-wop choir during a pair of 2009 concerts at New York’s Beacon Theatre. If a convicted murderer could create a new life for himself, a maligned musical might someday be able to do the same.

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