Beset by financial woes that led to bankruptcy in 1993, Haggard had also run afoul of his record label boss Mike Curb.

Comparing If I Could Only Fly favorably to Bob Dylan's Time Out of Mind, Ryan Kearney of Pitchfork writes, "in listening to their reflections on aging and the accompanying doubts, we can learn how to face our own mortality with greater equanimity and fewer regrets.

All the songs emanate from a single persona, an aging, cloistered singer (Haggard is in his sixties) whose routine—avoiding drugs, taking comfort from cushioned bus seats, being honest with his kids — is all he has".

Stephen Thomas Erlewine of AllMusic wrote: "If I Could Only Fly is the first album in years that deserves to be compared to Haggard's classic work.

"[1] Music critic Robert Christgau wrote "After a long, dispiriting string of releases that gradually devolved from hit-or-miss to cynical, he comes out of nowhere on a punk label to cut one of the very best albums of his very uneven recording career.