Keith Whitley's 10 Best Songs: Critic's Picks

Keith Whitley
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Keith Whitley

Keith Whitley was one of the most-respected bluegrass pickers in the business when he decided to make a run at country music in the early 1980s. His first few projects for RCA were very much a mixed bag. There were some classic moments -- “Miami, My Amy” being a prime example, but radio took their time warming up to the singer.

The summer of 1988 changed that. “Don’t Close Your Eyes” was the record that he had spent a career looking for, and the next two follow-ups also topped the chart. He was married to fellow rising star Lorrie Morgan, and the sky seemed to be the limit for what should have been Nashville’s next power couple. But, their story -- and his career -- came to a tragic end on the morning of May 9, 1989. Though he left us too early, Whitley’s music -- like that of artists such as Patsy Cline and Hank Williams, both of whom died young -- will live on forever, inspiring countless artists that have come along since, such as Chris Young, and the man who moved to Nashville that same fateful day -- Tim McGraw. Here are 10 Keith Whitley song moments that those artists, as well as his fans, will love forever!

Best Songs: Alabama | Alan Jackson | Alison KraussBilly Currington | Blake Shelton | Brad Paisley | Brett Eldredge | Brett Young | Carrie Underwood | Chris Stapleton | Clint BlackConway Twitty | Cole Swindell | Darius Rucker | David Allen CoeDierks Bentley | Dixie Chicks | Dolly Parton | Dwight Yoakam | Eric Church | Faith Hill | Garth Brooks | Gary AllanGeorge Jones | George Strait | Glen Campbell | Hank Williams Jr. | Jason Aldean | Johnny Cash | John Denver | Justin Moore | Keith Urban | Kelsea Ballerini | Kenny Chesney | Kenny Rogers | Lady Antebellum | Little Big TownMartina McBride | Merle Haggard | Miranda Lambert | Patsy Cline | Randy Travis | Rascal Flatts | Reba McEntire | Sam Hunt | Shania Twain | Sheryl Crow | Thomas Rhett | Tim McGraw | Toby Keith | Travis Tritt | Vince Gill | Waylon Jennings | Willie Nelson | Zac Brown Band

10. Earl Thomas Conley feat. Keith Whitley - "Brotherly Love"

Whitley recorded his vocals on the track back in 1987, but the song stayed unreleased until RCA issued the track as the lead single from his Kentucky Bluebird disc. The tune also represented the final major hit for Conley, who was one of the top male vocalists of the 1980s.

9. Keith Whitley - "Homecoming '63"

Veteran songwriters Dean Dillon and Royce Porter collaborated to pen this emotional record for Whitley, which became his second top 10 hit. The song is also notable for its nostalgic video featuring Whitley and wife Lorrie Morgan in a romantic moment.

8. Keith Whitley - "When You Say Nothing At All"

Whitley's star continued to rise in 1988 with a second straight chart-topper from Don’t Close Your Eyes, which was written by the white-hot team of Don Schlitz and Paul Overstreet. His heartfelt performance on the ballad made for one of the top moments on country radio in the holiday season of 1988-89. At the time, it seemed like there would be many more trips to the top for Whitley, but fate had other plans.

7. Keith Whitley - "Til’ The Tear Becomes A Rose"

Released a year after his passing, this tender performance between Whitley and Morgan became a fan favorite, while also causing them to ask the question of what could have been. Surely, there would have been other collaborations between the two, but this song -- and their three year union -- would prove to be their Camelot.

6. Keith Whitley - "Would These Arms Be In Your Way"

One could say that country radio rejected this haunting ballad, as it only peaked at No. 36 in the fall months of 1987. However, that only tells half of the story. The song has been covered almost as many times as any other in the Keith Whitley song catalog, and...anytime you include the vocals of Vern “The Voice” Gosdin and the timeless Emmylou Harris, you’ve got a classic recording -- and one that deserves a place on this list -- chart position be damned!

5. Keith Whitley - "I Wonder Do You Think Of Me"

The first single issued by RCA after his passing, this song might not have had the impact that it did if Whitley had outlasted his demons. That’s not a knock on the Sanger D. Shafer-written gem, but the lyrics combined with his passing made for one of the most haunting performances in country music history. Fans were still numb with grief when this song was issued during Fan Fair 1989, and the sad nature of this song made the wound even more real.

4. Keith Whitley - "Miami, My Amy"

Granted, Whitley’s first major hit wasn’t even a Top 10 entry, peaking at No. 14, but Blake Mevis’ production -- which was the most pop-sounding of his career -- only seemed to accentuate his traditional Kentucky leanings. And, having a song from the collective pen of Dillon and Porter -- along with Country Music Hall of Famer Hank Cochran -- certainly didn’t hurt!

3. Keith Whitley - "Don’t Close Your Eyes"

After the success of his first album, Whitley went to work on album number two. However, when he took the record to RCA exec Joe Galante, he realized that it wasn’t quite what he wanted it to be, and asked to scrap the record. Galante -- in a move that likely wouldn’t be allowed today -- allowed Whitley to do just that, and paired him with Garth Fundis, who produced the record. Fundis’ first task was to find a hit that would define Whitley’s direction. This Bob McDill number about a man who is pleading with his lover to let go of the ghosts from a previous relationship -- and love him for who he is -- was just the right recipe, making it the first of four No. 1 Keith Whitley songs.

2. Keith Whitley - "I’m Over You"

The final solo top 10 from Whitley was another song that tended to take on a new meaning after his death. Released as the third single from I Wonder Do You Think Of Me, this song mirrored George Jones’ “He Stopped Loving Her Today,” making it an essential moment in his catalog.

1. Keith Whitley - "I’m No Stranger To The Rain"

Though few in Music City were aware of just how deep Whitley’s demons ran in his life, the singer never tried to deny that they were there. He battled depression as well as alcoholism during his life, and nobody will ever know how his newfound fame affected those. In this emotionally riveting track seemed to be his story -- though he didn’t write it. It turned out to be more prophetic than anyone knew. The song hit No. 1 on April 8, 1989 -- and one month and a day later, Whitley was gone.