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On June 25, 2019, The New York Times Magazine listed Patty Loveless among hundreds of artists whose material was reportedly destroyed in the 2008 Universal fire.

Roger Ramey sent the demo tape out to every major label in Nashville, and was met with a solid wall of rejection by them all. After a month of not getting anywhere, out of desperation to help his sister, he decided to take a chance with MCA Nashville. MCA, being the industry leader at the time was his first choice of labels. Taking a cassette of the five song demo of Loveless, Roger bluffed his way past the receptionist of Tony Brown, the head of A&R (Artist & Repertoire – in charge of finding and developing new talent) by pretending to be someone else who was late for an appointment.

In 1995 Lovelesss sang background vocals on the Vince Gill recording Go Rest High On That Mountain. The song won the CMA's Song of the Year award in 1996 and a BMI Most-Performed Song award in 1997. It also received two Grammy Awards for Best Male Country Vocal Performance and Best Country Song in the 38th Grammy Awards. The single reached No. 14 on the Country Singles chart in 1995. It has sold 648,000 digital copies in the US since becoming available for download. On May 2, 2013, Loveless performed the song with Gill at the funeral of fellow country artist George Jones. At one point during the performance, Gill became too emotional to sing some of the words, but was able to complete the song by focusing primarily on his guitar playing. In a speech just prior to Gill's and Loveless' performance, Gill underlined their duet by stating that he always was aware of a "special anointing" in his duets with Loveless, and compared them particularly to Jones' duets with singer Melba Montgomery during the 1960s.

She took a two-year sabbatical from touring in 2006 and 2007 to heal from the loss of her mother & mother-in-law and enjoy home life with husband Emory Gordy, Jr., though she & Gordy performed several times at the Grand Ole Opry and did a couple of guest appearances at other shows. In 2007, Loveless was also a judge for the 6th annual Independent Music Awards to support independent artists' careers. Loveless was inducted into The Kentucky Music Hall of Fame on April 7, 2011.

Returning to the studio in 2008, Loveless appeared on a track on George Strait's Troubadour album, as well as a track on Jimmy Wayne's Do You Believe Me Now. Later in 2008, Loveless signed a recording contract with Saguaro Road Records., and recorded a Tribute album, Sleepless Nights, which was released on September 9. Sleepless Nights received a Grammy Award nomination for Best Country Album. Patty's latest recording for Saguaro Road, Mountain Soul II, was released on September 29, 2009, which would go on to win a Grammy for Best Bluegrass Album.

Loveless resumed touring in September 2008 with a handful of appearances and continued touring with small annual tours in a few venues through 2010. She has been active as a background singer for a number of artists, appearing on Miranda Lambert's Four the Record (2011) and Kathy Mattea's Calling Me Home (2012).

After her release from Sony Nashville, in 2006 Loveless sang a duet with Bob Seger on his Face the Promise album, also collaborating with Solomon Burke on his Nashville album and performing a duet, "Out of My Mind", with Vince Gill on his album These Days. This was their first recorded duet since "My Kind of Woman, My Kind of Man", which they recorded in 1998.

In 2005, she released Dreamin' My Dreams. While critical reception was good, it did not fare well commercially. The album debuted and peaked at number 29 on Billboard's country album chart while no song from the album made the singles chart. This was the last album Loveless recorded for Epic Records before the label closed its Nashville division in 2005 and released Loveless from her recording contract.

In an effort to control her own destiny, rather than be controlled by country radio, Loveless made an abrupt move away from commercial, country/pop and made a stone-cold bluegrass album in 2001. Mountain Soul Soul was released to numerous critical accolades and sold decently despite a lack of radio support. She used the same bluegrass approach on a Christmas album, Bluegrass & White Snow: A Mountain Christmas, in 2002. On Your Way Home, a return to more commercial oriented country, was released in 2003 to critical acclaim. Though she has not scored a top-forty country single since "On Your Way Home" reached # 29 in 2004, Loveless' albums still do well, usually charting in the country albums top forty, despite the fact that she no longer has the support of mainstream country radio or a major label.

Perhaps her crowning achievement was that album's follow-up, When Fallen Angels Fly. That album won the Country Music Association's Album of the Year award and gave her four Top 10 singles. She followed it up with The Trouble with the Truth in 1996 which gave her Female Vocalist of the Year awards from both the Academy of Country Music and the Country Music Association.

In 1994, Loveless contributed the song "When I Reach the Place I'm Going" to the AIDS benefit album Red Hot + Country, produced by the Red Hot Organization.

On her 36th birthday, January 4, 1993, Loveless re-entered her professional life by performing at the Grand Ole Opry. She had fully recovered, although her voice was changed by the surgery. It had a deeper, fuller quality which enhanced her career over the following years.

Larry Fitzgerald, her new manager, believed a major change was in order. At the end of 1992, Fitzgerald met with Tony Brown to try to get Loveless out of her MCA contract. He worked out an agreement with MCA that Loveless could leave the label, but retained an option to record with other MCA artists on the MCA Label. Quickly, Fitzgerald arranged a meeting with Roy Wunsch, the head of Sony Nashville. Their Epic label was looking for a "name" female singer and worked out a contract for Loveless to record for Sony under their Epic label.

Despite the voice problem, Loveless had booked an autumn 1992 tour. Additionally, she had been invited to appear on a CBS television special Women In Country. The day before leaving on the tour, Loveless asked her manager to accompany her to her throat doctor's office. In the office, her doctor compared her 1990 results versus what he saw during the exam. Her vocal cords had developed an enlarged blood vessel that looked like a varicose vein. The juxtaposition was dramatic, and furthermore, if not treated, it could end her career and there was no guarantee that surgery could correct the problem.

Although Loveless went ahead and sang in the television special, her manager canceled all of her tour dates for the remainder of 1992. On October 21, Loveless had corrective throat surgery. For the next nine weeks, she could neither sing nor talk. Her husband, in order to communicate with her, attempted to teach Loveless Morse Code, as well as using pen and paper with yellow Post-It notes. After this, her interest in Amateur Radio developed and she was eventually licensed with the callsign KD4WUJ, although her license currently shows as canceled.

On Down the Line followed in 1990. This album produced four more singles for Loveless. The title track, also penned by Kostas, was first at No. 5 on the Hot Country Songs charts. Following it was a cover of Lucinda Williams' "The Night's Too Long", then "I'm That Kind of Girl" and "Blue Memories". Her final MCA studio album, 1991's Up Against My Heart, produced the Top 10 hit "Hurt Me Bad (In a Real Good Way)", while followup singles "Jealous Bone" and "Can't Stop Myself from Loving You", were less successful. Following the latter, she also sang a guest vocal on "Send a Message to My Heart", a single from Dwight Yoakam's If There Was a Way. Up Against My Heart included backing vocals from Dolly Parton, Vince Gill, Mac McAnally, and Lyle Lovett, who also wrote the final track "God Will".

With the new recording contract, Loveless headed into the recording studio to record new material for Epic. In the studio, her producer (Gordy) noticed that her voice was not as strong as it had been when she last recorded two years previously. The fact was that beginning as far back as 1990, Loveless felt some pain in her throat when singing, and when she saw a physician, he noticed a red spot on her vocal cords. By 1992, Loveless was on a regimen of steroid tablets and cortisone to prop up her voice.

Although Loveless continued to record for Epic throughout the 1990s and into the early 2000s, her commercial momentum slowed down, as neo-traditionalist artists like Loveless were eclipsed on country radio by flashier, trendier young performers like Shania Twain and Faith Hill; none of the singles released from her 1997 album Long Stretch of Lonesome or 2000's Strong Heart reached the top ten. (The albums themselves continued to do well, however, with Long Stretch reaching # 9, and Strong Heart peaking at No. 13 on the country albums charts.)

In February 1989, Loveless and Gordy secretly married in Gatlinburg, Tennessee. For a year and a half afterward, they publicly hid the fact that they were married, in large part because Loveless did not want to hurt her former husband, Terry Lovelace, who still loved his former wife and hoped to rejoin her.

Loveless has charted more than 40 cuts on the Billboard Hot Country Songs charts, including five in the No. 1 position: "Timber, I'm Falling in Love", "Chains", "Blame It on Your Heart", "You Can Feel Bad", and "Lonely Too Long". She has recorded 14 studio albums (not counting compilations); in the United States, four of these albums have been certified platinum, and two have been certified gold by the Recording Industry Association of America (RIAA). She has been a member of the Grand Ole Opry since 1988. Loveless was married to Terry Lovelace, from whom she derived her professional name, from 1976 to 1986. She has been married to record producer Emory Gordy Jr. since 1989.

It was her second album, If My Heart Had Windows, released on January 25, 1988, was the one that got Loveless noticed in the country music world. "If My Heart Had Windows" and "A Little Bit in Love", covers of George Jones and Steve Earle respectively, both reached the country music top 10. Also, in 1988 Loveless was invited to join the Grand Ole Opry, which put her firmly in Nashville to stay. On the road, Loveless was the opening act for the top MCA artists, such as George Jones, Reba and Strait, which had people coming early to the shows to hear her sing. However, her concert popularity did not translate into album sales for her label.

Loveless' second single, "I Did", was released in April 1986. The song had gone out with releases from four other MCA singers, all of whom had album contracts. Shortly after its release, Roger Bowen asked Loveless to come into his office where he explained to her that he wanted to pull the song from radio because it was succeeding too well. "I have to be fair to the other artists". In return, he would give Loveless an album deal and she could release "I Did" as a single from her first album. This produced the self-titled Patty Loveless album, being initially released on October 1, 1986 in a promotional form, with a full release on February 21, 1987. The singles, "Wicked Ways" and "After All", were released from that album, which again, did not do well on the charts but garnered sufficient airplay that Tony Brown decided to sign Loveless to a long-term recording contract.

In April 1985, Loveless felt her marriage to Terry Lovelace was ending (they eventually divorced amicably in 1986). She contacted her brother Roger to help her get back to Nashville. After being in the rock 'n' roll scene for so long she felt completely out of the country-music loop but wanted to sing country music again. Roger Ramey helped his sister cut a five-song demo tape, one of them being a rough cut of her self-penned song "I Did", which Loveless first wrote as a teenager, then later included on her first album. Roger Ramey then began to spread the word around about her talent. She and her brother disagreed about including "I Did" on the demo tape. Loveless didn't believe the song was good enough, but Roger argued that it would be what got her a contract. Once the demo was finished, Roger started trying to get her a recording contract with a major label in Nashville.

Tony Brown brought in one of his top producers, Emory Gordy Jr., to help develop Loveless for MCA. Together, they produced a series of songs for Loveless, and all of them were released to radio stations with varying degrees of success. MCA released her first single, "Lonely Days, Lonely Nights" on December 7, 1985, charting on the Billboard Hot Country Songs chart for 8 weeks, reaching No. 46 on January 25, 1986.

The years in North Carolina were not successful for her, as the police started busting the clubs she would perform in and shut them down. When she wasn't performing she was working as a waitress at her mother-in-law's restaurant. By 1984, she was singing in a club and was singing country music for a change of the rock she would normally perform. There was a new generation of artists in Nashville, singers like George Strait and Reba McEntire who were changing the traditions of country music.

During this time of her life she also was distant from her family, as she had married without their consent. According to Loveless, "...I think my father thought I had lost my mind. This music is going to just ruin your life... it ruined your life... But it was a music that I learned from again... You wouldn't believe the people that would come to this club. They would get off from work, and they wouldn't go home. They'd come to this club and have a few beers, or ... dance.... I learned a lot about people and life in those places. I mean there was all walks of life... people who had hit the very bottom. And myself, there was times I felt myself becoming one of those people too. There was some hard times for us both, my ex-husband and I. And I think at the time, it caused us to be torn apart, and we lost respect for each other. And it got to the point that we didn't know each other..." A low point of her life was in October 1979, when her father, whom she idolized, died near Louisville while Loveless was in North Carolina.

Loveless graduated from Fairdale High School in 1975. Her older sister, Dottie Ramey, an aspiring country singer, frequently performed at small clubs in eastern Kentucky with her brother Roger, billed as the Swinging Rameys. Traveling with Dottie and Roger to Fort Knox in 1969 and hearing her sister perform on stage, Patty Ramey decided that she would like to become a performer as well.

After graduation from Fairdale High School in Louisville, Kentucky, in 1975 Patty Ramey became a full-time member of the Wilburn Brothers' band as their lead female singer. About this time she met the Wilburns' new drummer, Terry Lovelace. Lovelace came from a small town in western North Carolina, Kings Mountain, and shared many things in common with Loveless. At first Patty kept her friendship and her growing relationship with Lovelace a secret from the Wilburns. However, eventually Doyle Wilburn learned about it and asked Patty to break it off. However, Ramey, being the rebellious teenager, instead quit the Wilburns and left with her boyfriend for western North Carolina. In early 1976, she married Terry Lovelace and began performing with him in a pickup-band based in Kings Mountain.

In 1973 Bill Anderson, Connie Smith, the Wilburn Brothers, and Jean Shepard were scheduled to appear in a touring Grand Ole Opry show in Louisville Gardens. However, Jean Shepard was caught in a flood, and she wasn't able to make it in. Danny King, sensing an opportunity, gave the Rameys a call. Loveless and her brother Roger appeared in the show for about 15 minutes on stage.

The Wilburn Brothers listened to Patty Ramey and after her performance asked her if she had ever sung professionally. She explained that she had worked with Porter Wagoner some and had traveled with him and Dolly Parton on weekends and during the summers. Doyle Wilburn asked if she wanted to come to Nashville and work with their band to replace their female singer, to which Patty Ramey agreed. Between 1973 and 1975 Patty Ramey traveled with the Wilburns on weekends and during the summers when school was out. Loveless's parents insisted that the Wilburns watch over her while on the road.

It was her brother Roger who initially took Patty Ramey to Nashville, Tennessee, in 1971. Having grown up listening to the music of the Grand Ole Opry both in Pikeville, and then in Louisville, Roger had moved to Nashville in 1970 and became a producer with The Porter Wagoner Show.

Loveless's interest in music started when she was a young child. In 1969, when she was 12, the Ramey family moved to Louisville, Kentucky. The move was necessitated from her father's struggles with Coalworker's pneumoconiosis, or black lung disease. This was caused by years of working in the coal mines and breathing in the coal dust.

When Dottie married in 1969 and quit performing, Roger persuaded Patty to perform onstage for the first time at a country jamboree in Hodgenville, Kentucky. The forum consisted of foldout chairs in a small auditorium and was called the "Lincoln Jamboree". She was terrified at first, but with her brother performed several songs; she loved the applause she received for her performance, and after the show she was paid five dollars, the first money she ever earned.

Patricia Lee Ramey (born January 4, 1957), known professionally as Patty Loveless, is an American country music singer. Since her emergence on the country music scene in late 1986 with her first (self-titled) album, Loveless has been one of the most popular female singers of neotraditional country. She has also recorded albums in the country pop and bluegrass genres. Loveless was born in Pikeville, Kentucky, and raised in Elkhorn City, Kentucky, and Louisville, Kentucky. She rose to stardom thanks to her blend of honky tonk and country-rock and a plaintive, emotional ballad style. Throughout her career, Loveless has sold 15 million albums worldwide.

Patty Loveless was born January 4, 1957, in Pikeville, Kentucky. She was the sixth of seven children born to Naomie (née Bowling; 1921 – 2006) and John Ramey (1921 – 1979) of Elkhorn City, Kentucky. Like many men in the area, Mr. Ramey worked as a coal miner.