Whitley was born to Faye (editor of The Elliott County News) and Elmer Whitley (an electrician) in Ashland, Kentucky, but was raised 46 miles away in Sandy Hook, and attended Sandy Hook High School. He had two brothers, Randy and Dwight, and a sister, Mary. The Whitley family has lived in the Elliot County area since the 1840s.  As a teenager in Sandy Hook, Whitley and his friends would pass the time drinking bootleg bourbon and racing their cars down mountain roads at dangerous speeds. Whitley was once in a car whose driver attempted to round a curve at 120 mph. The car wrecked, killing his friend and almost breaking Whitley’s neck. In another incident, he drove his car off a 120-feet cliff into a frozen river, escaping with only a broken collar bone.

In 1969 he performed in a musical contest in Ezel, Kentucky, with brother Dwight on five-string banjo. Ricky Skaggs was also in the contest. Skaggs and Whitley hit it off right away and quickly befriended each other.  As teenagers, Whitley and Skaggs  were discovered in Ft. Gay, WV by Ralph Stanley who was 45 minutes late due to a flat tire. Ralph was in a bad mood and when he opened the door of the club he heard the Stanley Brothers playing on what he figured was a jukebox. He said it was two young gentlemen who “sounded just like me and Carter in the early days”. [Keith became lead singer for Ralph after Roy Lee Centers funeral in 1974 in a diner] The two soon joined Ralph’s band. Whitley also played with J.D. Crowe & the New South in the mid-seventies. During this period, he established himself as one of the most versatile and talented lead singers in bluegrass. His singing was heavily influenced by Carter Stanley and Lefty Frizzell. He moved to Nashville in 1983 to pursue a country music career and soon signed a record deal with RCA Records. Whitley’s first solo album, A Hard Act to Follow, was released in 1984, and featured a more mainstream country style. While Whitley was working hard to achieve his own style, the songs he produced were inconsistent. Critics regarded the album as too erratic. Whitley honed his sound within the next few years for his next album, L.A. to Miami.

L.A. to Miami, released in 1986, would give him his first Top 20 country hit single, “Miami, My Amy”. The song was followed by three more hit songs: “Ten Feet Away”, “Homecoming ’63”, and “Hard Livin'”, The album also included “On the Other Hand” and “Nobody in His Right Mind Would’ve Left Her”. “On the Other Hand” was pitched to Whitley before Randy Travis released the song as a single and when Whitley’s version wasn’t released as a single, Travis released his in 1986, as did George Strait with “Nobody in His Right Mind Would’ve Left Her”.  During his tour to promote L.A. to Miami, he met and began a romantic relationship with country singer Lorrie Morgan. The pair were married in November 1986, and they had their only child, a son, Jesse Keith Whitley, in June 1987. Whitley also adopted Lorrie’s daughter, Morgan, from her first marriage.

During the new recording sessions in 1987, Whitley started feeling that the songs he was doing were not up to his standards, so he approached RCA and asked if the project of 15 songs could be shelved. He asked if he could assert himself more with the songs and production. The new album, titled Don’t Close Your Eyes, was released in 1988, and the album sold extremely well. The album contained one of the many songs that Whitley had a hand in writing in his years at Tree Publishing, “It’s All Coming Back to Me Now.” Also on the album was a remake of Lefty Frizzell’s classic standard “I Never Go Around Mirrors,” and the song became a huge hit at Whitley’s concerts. The first three singles from the album—”When You Say Nothing at All,” “I’m No Stranger to the Rain,” and the title cut—all reached number 1 on Billboard Magazine’s country charts during the fall of 1988 and the winter of 1989, with the title track “Don’t Close Your Eyes” being ranked as Billboard’s No. 1 Country song of 1988. Shortly thereafter, “I’m No Stranger to the Rain” also earned Whitley his first and only Country Music Association award as a solo artist.  In early 1989, Whitley approached Sony Music Nashville chairman Joe Galante with the intention of releasing I Never Go Around Mirrors as a single. Galante approved of the musical flexibility that Whitley achieved with the song; however, he suggested that Whitley record something new and more upbeat. The result was a song Whitley had optioned for his previous album called I Wonder, Do You Think of Me?, and was to result in his next album release.

Whitley was a longtime alcoholic, who started drinking early in his career at bluegrass gigs, long before he was legally allowed to drink alcohol. Many times he had tried to overcome his alcoholism, but failed; and his pre-existing depression made it more challenging for him to quit. Whitley preferred to drink alone, making it difficult for anyone to detect that he had a problem. According to Lorrie Morgan, she tried to conceal all alcoholic beverages from him at the home they shared, even going to the extent of binding hers and Whitley’s legs together before going to bed so as to make it impossible for Whitley to wake up in the middle of the night to consume a drink without her knowledge – only to discover that he would drink things such as perfume and nail polish remover to get intoxicated.  Whitley had lost both his father Elmer in 1987 and his brother Randy in an October 1983 motorcycle accident, five years before his death.  On the morning of May 9, 1989, after a weekend of drinking and partying, Whitley awoke and spoke with his mother briefly on the phone. He was then visited by his brother-in-law Lane Palmer, and the two had coffee and they were planning a day of golf and having lunch, after which Whitley had planned to start writing songs for Lorrie Morgan and himself to record when she returned from her concert tour. Palmer departed at approximately 8:30 a.m., informing Whitley to be ready to leave within an hour. Upon returning, Palmer found Whitley face down on his bed, fully clothed.

The official cause of death was determined to be acute ethanolism (alcohol poisoning), and Davidson County Medical Examiner Charles Harlan stated that his blood alcohol level was .47 (the equivalent of 20 1-ounce shots of 100-proof whiskey and almost five times the then Tennessee level of .10 legal intoxication limit, and nearly six times the current .08 legal limit to drive). Whitley was 34 years old.  The day after his death, Music Row was lined with black ribbons in memory of Whitley. He is buried in the Spring Hill Cemetery outside Nashville, Tennessee.

It has long been speculated that Whitley’s death may not have been directly caused by his recklessness or alcoholism, but that he may have been a victim of premeditated misconduct. In 2009, forensic pathologist and then-chief medical examiner Charles W. Harlan stood trial for several cases of forensic fraud which led to the misdiagnoses of several deceased patients, and possibly the conviction of innocent people under suspicion of murder. Subsequently, the man who originally laid claim that Whitley’s death was solely by alcohol poisoning has been relieved of his license to practice pathology. Whitley’s death certificate and autopsy results had once been sealed from public access, but have since been made public record.

Despite Whitley’s death, his influence on country music has persisted long after his death. At the time of his death, he had just finished work on his fourth and final studio album, I Wonder Do You Think of Me. The album was released three months after his death, on August 1, 1989. The album produced two more No. 1 hits, with the title track and “It Ain’t Nothin’.” “I’m Over You” also saw the Top 5 in early 1990, reaching No. 3.  Two new songs were added to “Greatest Hits”: The first, “Tell Lorrie I Love Her” was written and recorded at home by Whitley for Morgan, originally intended as a work tape for Whitley’s friend Curtis ‘Mr. Harmony’ Young to sing at Whitley’s wedding. The second was “‘Til a Tear Becomes a Rose”, a 1987 demo taken from Tree that originally featured harmony vocals by childhood friend Ricky Skaggs. Lorrie Morgan, with creative control and license to Whitley’s namesake, recorded her voice alongside Whitley’s, and released it as a single, which rose to No. 13 and won them 1990’s CMA award for Best Vocal Collaboration.  RCA also released a compilation of performance clips (from his days in the Ralph Stanley-Fronted Clinch Mountain Boys), interviews, and some previously unreleased material under the title “Kentucky Bluebird”. The album produced hits for Whitley as well, including a duet with Earl Thomas Conley, named “Brotherly Love,” which peaked at No. 2 in late 1991.

In 1994, Whitley’s widow, Lorrie Morgan, organized several of Whitley’s friends in bluegrass and some of the big names in country at the time to record a tribute album to Whitley. The album, Keith Whitley: A Tribute Album, was released in September 1994 via BNA. It included covers of Whitley’s songs from artists such as Alan Jackson, Diamond Rio, and Ricky Skaggs. The album also includedfour previously unreleased tracks recorded by Whitley in 1987, one of which had Morgan dubbed in as a duet partner. The album also included two original songs: “Little Boy Lost”, co-written and sung by Daron Norwood, and “A Voice Still Rings True”, a multi-artist song. Alison Krauss’s rendition of “When You Say Nothing at All” was released as a single from the album, reaching number 3 on the country charts in 1995.  In 1995, the album Wherever You Are Tonight was released, produced by Lorrie Morgan, featuring restored demos of 1986-1988, with crisper 1990s recording techniques and a full orchestra. The album and single of the same name both did very well on the Billboard and R&R charts and brought “Super Hits” and “The Essential Keith Whitley” in 1996. “The Essential” contained the remastered and long since unavailable LP and Whitley’s debut, the 6-Track “A Hard Act to Follow”, and a scrapped song from 1986’s “LA to Miami”, “I Wonder Where You Are Tonight”.

In 2004, songwriter Jeff Swope began writing a film treatment for a biopic concerning Whitley’s life and death that was shelved in 2006. On April 13, 2010, he announced that pre-production was set to begin again, pending investors.  In the last 10 years, several film projects depicting Whitley’s life were slated. One idea was a film version of the George Vescey-Lorrie Morgan-penned “Forever Yours, Faithfully”. While Morgan’s book was a benchmark in piecing together Whitley’s final moments, perhaps the most research went into a project titled “Kentucky Bluebird”, which was to star writer/actor/director David Keith. This project has been in development hell for several years, and was halted in late 2006 also, after difficulties with casting and funding.