Although best known as a songwriter and alternative country artist, Crowell enjoyed mainstream popularity during the
late 1980s and early 1990s.
His critically acclaimed album, 1988's Diamonds & Dirt,
produced five No. 1 hits during a 17-month span in 1988 and 1989: "It's Such a Small World" (a duet with Cash),
"I Couldn't Leave You If I Tried," "She's Crazy for Leaving," "After All This Time" and
"Above and Beyond."
His follow-up album, 1989's "Keys to the Highway,"
produced two top 5 hits in 1990, which were "Many a Long and Lonesome Highway" and "If Looks Could Kill."
As Crowell's popularity in hit-radio country music faded, he continued his prolific songwriting. In 2001, he released
The Houston Kid on Sugar Hill Records. Many songs on the album were semi-autobiographical, and the album included a duet with
Crowell's ex father-in-law Johnny Cash on "I Walk the Line (Revisited)". Initially, Cash was annoyed at Crowell
changing the tune to his song, but he came to like the finished product.
Crowell followed up
this effort with Fate's Right Hand in 2003 and The Outsider in 2005, both of which came out on Columbia Nashville, a division
of Sony Music. Leading critics and Crowell consider these three albums his finest work as a solo artist.
2004 saw the
release of The Notorious Cherry Bombs, a reunion of Crowell's 1970s road band, which included Vince Gill, Tony Brown and
others. The future Keith Urban hit "Making Memories of Us" was included on this disc. In 2005, Crowell served as producer
for established Irish singer/songwriter Kieran Goss on the album Blue Sky Sunrise.
In 2008 CMT announced that
Crowell's next album, Sex and Gasoline, would come out on Yep Roc Records, ending his relationship with Sony Music. This marked
the first time Crowell did not produce his CD. The album was nominated for a Grammy in the category of Best Contemporary