The Meaning Behind “A Bad Goodbye,” the Gut-Wrenching Duet by Clint Black and Wynonna

Seinfeld fans know that Elaine Benes once was victimized by a “bad breaker-upper,” a guy who was so insulting to the women who were separating from him that he inspired violent retribution. The narrator of “A Bad Goodbye,” written by Clint Black and sung in a mesmerizing duet by Black and Wynonna at the height of their respective popularities in 1994, gets the break-up process right—and breaks our hearts in the process, too.

What did Clint Black have in mind when he wrote this beautiful ballad? And what kind of second life did it receive when it was used to send off a fictional talk show host? Read on to find out all the details of one of the best country duets you’ll ever hear.

In Like Clint

In an era filled with country mega-stars, Clint Black’s track record of success could hang with just about anybody in the genre. The guy came right out of the gate with four straight country No. 1 singles from his 1989 debut album, Killin’ Time. Doubly impressive was the fact that, on a vast majority of his songs, Black was either the sole writer or co-wrote them with Hayden Nicholas. In other words, he didn’t need any Nashville songwriting committees to put him across.

In 1993, Black released No Time to Kill, his fourth album. For the lead single, he decided on “A Bad Goodbye,” a ballad he wrote by himself. And for the first time ever on one of his albums, he asked a guest to duet with him. What a duet partner he found: Wynonna Judd, who had left The Judds in 1991 and was in the midst of her own incredible string of solo chart successes.

[RELATED: Michael Ray Interviews Clint Black for American Songwriter]

As far as the writing of “A Bad Goodbye,” Black found that putting himself inside the character who might be going through the situation the song describes provided the spark, as he told American Songwriter in 2004. “When I started to think about it, I found the sadder meaning of a bad goodbye, and started thinking, ‘OK, if we’re going to the sad part and somebody’s leaving with a bad goodbye or not wanting to leave, there must be still some love there,’” he explained. “I started thinking about what I would be feeling, and then the song began writing itself and things came out that were real.”

“A Bad Goodbye,” which featured Wynonna singing the first middle-eight and then harmonizing throughout the rest of the song, continued Black’s run of success when it was released, hitting No. 2 on the country charts and denting the Top 50 in the pop charts, as well (the first of his songs to ever do so). A few years later, the song was given a new lease on life from an unexpected source. Keep reading to find out what it is, but here’s a little hint: “No flipping.”

Hats Off to Larry

“No flipping” was the catchphrase that the fictional TV talk show host Larry Sanders would use going to a commercial, essentially urging his viewers to stay with the show. Sanders was played by Garry Shandling, who, like his alter ego, was a comedian and late-night host himself. The Larry Sanders Show played for six critically-acclaimed seasons on HBO in the ‘90s, at the same time Black was standing atop the country world.

Black met Shandling when the latter was hosting the Grammys one year, and the two hit it off and became buddies. The country star appeared in one episode as one of Sanders’ guests. When the show was heading off the air in 1998, the plot featured Sanders hanging up his show as well. Shandling asked Black to return and perform “A Bad Goodbye,” and his tender performance proved to be a memorable part of one of the finest TV series finales ever.

What Is “A Bad Goodbye” About?

The title is actually misleading, because the narrator is doing his darndest to ensure that his parting of the ways with his about-to-be-ex is rendered as benignly as possible. There’s no hope for a turnaround of any sorts, as we find out in the opening lines: I’ve been bound to leave you / We’ve known that for a while. Even though he knows a clean break is necessary, he doesn’t want her to feel the pain such a move would cause her: My heart won’t let me put you through / What my mind said should happen now.

The bridge features marvelous, seemingly simple rhymes that ingeniously amplify the impossibility of the narrator’s plight, while the wordplay picks at the fact that an English word representing an oft-devastating event is partly comprised of a benevolent adjective: 

Goodbye, easier said than done
Goodbye, there’s no good when you’re the one
Whose goodbye you swore would never come
And in my goodbye you’re finding none

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Black and Judd sum it up again and again with the refrain of I can’t leave you with a bad goodbye. The song ends without us finding out if the narrator was actually able to finesse the situation in such a way that both parties leave with their hearts and their dignities intact. It’s the heartbreak that comes along with his attempt to do so that makes “A Bad Goodbye” such a resonant weeper. If only Elaine Benes could have met this guy.

Photo by Ethan Miller/Getty Images for dcp

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