Country Hall of Fame Songwriter Dean Dillon's 10 Greatest Songs

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by Julian Spivey
Last week songwriter Dean Dillon was elected to the Country Music Hall of Fame in the Songwriter category, which rotates yearly with the Non-Performer and Recording/Touring Musician categories. Dillon has been one of country music best and most acclaimed songwriters since the early ‘80s and his music has become synonymous with Country Music Hall of Fame performer George Strait, who has cut many of Dillon’s songs. Strait has cut 55 songs written or co-written by Dillon and 11 of those reached No. 1 on the country charts. Dillon has also written classics for the likes of George Jones, Vern Gosdin and Keith Whitley.

Here are Dean Dillon’s 10 greatest songs … 

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10. Nobody in His Right Mind Would’ve Left Her
“Nobody in His Right Mind Would’ve Left Her,” a solo write for Dean Dillon, was first released as a single by Dillon himself in 1980 and proved to be the most successful single he’d release as a recording musician when it went to No. 25 on the country chart. The heartbreaking ballad of a man who foolishly broke up with his girlfriend only to later regret it was the perfect song for George Strait’s suave crooner era in the mid-‘80s when he was recording stuff like this, “It Ain’t Cool to Be Crazy About You” and “The Chair” (all written or co-written by Dillon). Strait would take “Nobody in His Right Mind Would’ve Left Her” to No. 1 in 1986. The song contains one of Dillon’s best lines in “even my heart was smart enough to stay behind.” 

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9. A Lot of Things Different
I remembered thinking almost 20 years ago now and still to this day whenever I hear it that “A Lot of Things Different,” written by Dean Dillon and fellow Country Music Hall of Fame songwriter Bill Anderson, should’ve been a bigger hit for Kenny Chesney. The nostalgic song about a man wishing he had made a lot of different decisions in his life did go all the way to no. 6 on the country singles chart for Chesney in 2002, but it doesn’t seem its had lasting power or will be remembered as one of his “greatest hits,” despite being one of the best he’s ever recorded. 

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8. I’ve Come to Expect It from You
“I’ve Come to Expect It from You,” written by Dean Dillon and Buddy Cannon, is one of George Strait’s dozens upon dozens of no. 1s. The song spent five weeks on top of the country singles chart at the end of 1990 and beginning of 1991. It’s a unique take on a breakup song in which the narrator isn’t even surprised his woman has walked out on him, because he’s come to expect that kind of thing from her. 

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7. Miami, My Amy
With a title like “Miami, My Amy” and the key lyric being, “Miami, My Amy loves me after all,” everything was ripe for this song written by Dean Dillon, Hank Cochran and Royce Porter, and recorded by Keith Whitley to be a stinker. Maybe it has much to do with Whitley’s perfect country music vocal, but the tale of a man who finds a love in Miami only to have to go back to L.A. (similar to “Marina del Rey” also co-written by Dillon) just works. I’ll still hear the track frequently on my local ‘80s, ‘90s and early ‘00s country radio station, but surprisingly it wasn’t even a top-10, topping out at No. 14 in 1986. 

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6. Unwound 
As mentioned at the top Dean Dillon has written an incredibly 55 songs recorded by the legendary George Strait and it’s a musical relationship that started at the very beginning of Strait’s hall of fame career. Dillon and Frank Dycus wrote the very first single ever released in Strait’s career in 1981’s “Unwound,” which set the man often called “King George” on a multiple decade’s long spree as country music’s biggest and best hitmaker. “Unwound” is an all-time great country music drinking song with the narrator going out on the town for a drink or many after being kicked out of the house by his woman when she catches him messing around. 

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5. Set ‘em Up Joe
“Set ‘em Up Joe,” written by Dean Dillon, Hank Cochran, Buddy Cannon and Vern Gosdin, and performed by the golden voiced Gosdin is both one of the greatest country music drinking songs of all-time, as well as one of the genre’s greatest tributes. The track is a tribute to the legendary Ernest Tubb, one of country music’s first superstars, with the song’s narrator sitting at a bar drinking beer and filling the jukebox with quarters to play “Walking the Floor Over You” all night long while forgetting an ex. Gosdin took the song to No. 1 in 1988. 

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4. Marina del Rey
“Marina del Rey,” co-written by Dean Dillon and Frank Dycus, is one of the most beautifully heartbreaking country songs ever written and recorded. Dillon and Dycus had written “Unwound,” the first ever single George Strait cut on his 1981 debut Strait Country, which went to No. 6 on the country chart (and was No. 6 on this list) and also collaborated on this track, which would be the second single off Strait’s sophomore release Strait from the Heart, which would also top out at No. 6 on the charts. “Marina del Rey” tells the tale of a man who met a woman while on vacation in Marina del Rey and the couple had the time of their life before having to go their separate ways and return to their normal lives in the real world. Strait’s vocal on the song is one of his career best. 

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3. Ocean Front Property
After the success of “The Chair,” Dean Dillon and Hank Cochran would reunite (along with Royce Porter) to write another No. 1 hit for George Strait, “Ocean Front Property,” the first single off Strait’s 1987 album of the same name. In a clever twist on a leaving lover’s impact on the narrator he wants to tell her he won’t be bothered by her leaving, before admitting that’s just not true and likening it to the impossibility of buying ocean front property in the state of Arizona. “Ocean Front Property” is witty and catchy, a specialty of Dillon’s that has shown up a few times in songs he’s written cut by Strait. 

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2. Tennessee Whiskey
The Dean Dillon song that’s arguably seen the most success and the most lives is “Tennessee Whiskey,” which he co-wrote with Linda Hargrove. The two decided to write a song together after meeting at Nashville’s famous Bluebird Café. The song was initially offered to George Strait, who turned it down (and I would assume regrets doing so), before first being cut by David Allan Coe on his 1981 album that shared its name with the track. Coe’s version wasn’t very successful, only topping at No. 77 on the country chart, but it caught the attention of the legendary George Jones who cut it on 1983’s Shine On and took it to No. 2 on the chart. Jones’ version would become a staple on classic country radio stations, but “Tennessee Whiskey” would see its most success when appearing on Chris Stapleton’s 2015 debut Traveller, especially after being performed as a duet with pop star Justin Timberlake on that CMA Awards that fall. That performance would propel “Tennessee Whiskey” to being a No. 1 hit nearly 35 years after its initially charting. 

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1. The Chair
George Strait has been the king of country cool when it comes to smooth-sounding love songs and none are likely as suave as the pickup line: “well, excuse me, but I think you’ve got my chair.” It’s a line from 1985’s “The Chair” off Strait’s Something Special album that Dean Dillon co-wrote with another legendary Country Music Hall of Fame songwriter Hank Cochran. This Strait No. 1 classic came at the end of a long night songwriting binge between the writers when Dillon strummed his guitar and sang the previously mentioned line. Within 20 minutes “The Chair” was complete.