It’s like, I told ‘em what I was gonna tell ‘em…I was tellin’ ‘em where I’d come from, the legacy and culture that shaped my music.”[3] He expanded to Country Music's Patrick Carr: "The first three albums were probably my need to express the cornerstones, my foundation musically and the things I first heard from my parents growing up in Ohio, the things they brought with them from Kentucky..."[4] If There Was a Way features the most diverse set of material Yoakam had recorded up to that point, introducing rock and soul influences while retaining the Bakersfield honky-tonk sound that made him famous.

The biggest departure is the title track, which incorporates a Hammond B-3 organ into the mix, giving the song more of a Muscle Shoals or Stax sound than Nashville or Bakersfield.

Roger would defer very quickly because he had a great internal artistic barometer, and he’s just one of the true giants in pop music writing.

"[8] Although If There Was a Way shows Yoakam's “fragmented musical personality",[6] it also contains unremittingly bitter and despairing country originals, such as “Sad, Sad Music” and the metaphorical “The Heart That You Own.” Although the latter only reached #18 on the country singles chart, it remains highly regarded (Bob Dylan covered the song in concert) and proved Yoakam could still write songs of heartache on par with previous classics like “Johnson’s Love,” “1,000 Miles,” and “I Sang Dixie.” A dominant theme found in Yoakam's new songs is the new aloofness or absence of a lover, as he croons on the bridge of "The Distance Between You and Me": On "Sad, Sad Music" the narrator declares, "I swear that I woke up with you this morning, but I can see that it's been days since you were here..." while "Nothing's Changed Here" contains the lines "I I feel you body lyin' next to mine, I reach out to touch you but you're not there for me to find..." Yoakam carries off these songs vocally with without a trace of irony, and the dark subject matter that dominates them, and the entire LP, may have played a part in his decision to conclude the album with the optimistic "Let's Work Together,' but, as Yoakam biographer Don McLeese writes, that particular cover song "served to show there were interpretive limits to what Dwight could do.

He was far more convincing brooding about dark nights of the soul than celebrating the brotherhood of man.”[9] The album's biggest hit was the ballad “You’re the One,” which reached #5 and was the final song from his 1981 demo session to be used for a major label release.

Thom Jurek of AllMusic calls “Since I Started Drinkin’ Again” (another old song played in Yoakam's 1986 set at the Roxy, which can be heard on the Rhino Deluxe Edition of Guitars, Cadillacs, Etc, Etc.)

“…a bluegrass shitkicker, but it is one hell of a self-destructive broken-heart song that features some awesome fiddlework by Scott Joss and mandolin and backing vocals by Tim O'Brien.” Album opener “The Distance Between You and Me” also incorporates banjo but, with its unconventional arrangement and exasperated lyrics, sounded downright surreal compared to most of what was on country radio in 1990.