1996-1997: All Because of You
A second album for Giant, All Because of You, was released in 1996. Its lead-off single "Amen Kind of Love" became his second No. 2 hit that year.
The album's other two tracks — "The Used to Be's" and "Even the Wind" — both fell short of Top 40, peaking at number 48 and 68 respectively.
1998-1999: Ain't It the Truth
Ain't It the Truth, his third and final album for Giant, produced a minor hit in "The Note", which peaked at No. 28 on the country charts and No. 90 on the Billboard Hot 100. Despite this song's minor crossover success, however, this album also saw its second and third singles miss the Top 40, and Singletary was dropped from Giant's roster.
2000-2001: Now and Again
In 2000, Singletary signed to Audium/Koch Entertainment to release his fourth album, 2000's Now and Again. This album's lead-off single was a cover of Savage Garden's 1999 pop single "I Knew I Loved You".
Following it were "I've Thought of Everything" at No. 70, and the album's title track, which failed to chart.
2002-2003: That's Why I Sing This Way
His second album for Audium/Koch, That's Why I Sing This Way, was mostly a cover album save for the title track. Both "That's Why I Sing This Way" and a cover of Conway Twitty's "I'd Love to Lay You Down" were released from this album, respectively reaching No. 47 and No. 43.