Kershaw was initially reluctant to release "Cadillac Style" because he felt that it was not suitable for his style; however, his co-producer, Buddy Cannon, convinced him to give the song a chance. Kershaw's often honky-tonk material and singing voice led to critical comparisons to George Jones, and he covered one of Jones's early singles, "What Am I Worth", on his debut as well. Kershaw's second album, Haunted Heart, followed in 1993. Its lead-off single, "She Don't Know She's Beautiful", became his only Number One hit, in April of that year. Following it were the title track, the Dennis Linde–penned "Queen of My Double-Wide Trailer", and "I Can't Reach Her Anymore", all of which hit the Top 10 as well. Although Kershaw had been told by others that radio audiences might not identify with the subject matter on "Queen of My Double-Wide Trailer", Kershaw wanted to release the song because he had an experience similar to its story line. Like his debut, Haunted Heart was a platinum album. In mid-1994, Kershaw also covered the Lynyrd Skynyrd song "I Know a Little" on the tribute album Skynyrd Frynds, which included country music covers of Skynyrd songs. Also in 1994, Kershaw contributed the song "Fire and Rain" to the AIDS benefit album Red Hot + Country, produced by the Red Hot Organization. Feelin' Good Train was Kershaw's third album, released later in 1994. This album also produced four hits, including two consecutive No. 2's in "National Working Woman's Holiday" and "Third Rate Romance" (the latter a cover of the Amazing Rhythm Aces hit from 1975), with the No. 27 "Southbound" and No. 18 "If You're Gonna Walk, I'm Gonna Crawl" following in 1995. The album included a duet with George Jones on "Never Bit a Bullet Like This", which had previously been released on Jones's 1993 album High-Tech Redneck. Feelin' Good Train was certified gold. It was followed by a Christmas album, Christmas Time's A-Comin', and Kershaw's first greatest-hits package, Greatest Hits, Volume 1, both in 1995. The latter produced a No. 47 single in "Your Tattoo" (written by Kostas and Jack Tempchin), the first single of Kershaw's career not to reach the Top 40. Mid-late 1990s Kershaw's fourth studio album, the gold-certified Politics, Religion and Her, was issued in 1996. It produced Top 10 hits in "Meant to Be" and "Vidalia", the latter of which Kershaw also considered a risky song, saying,