These posts are about the songs that fell just short of crossing the key line of chart success, entering the Billboard Top 40. Every song featured in this series peaked at number 41.

Bob Dylan logged seven Top 40 singles during a span beginning in 1965 and ending in 1970. Three of those songs made it into the Top 10, and two of fell just short of topping the chart. “Like a Rolling Stone” couldn’t overcome the Beatles’ “Help!,” and “Rainy Day Women #12 and 35” was boxed out by the Mamas and the Papas’ “Monday, Monday.” Despite a reputation as melodic bard who was too complex for the masses from the jump, Dylan started his career as a hitmaker.

During the nineteen-seventies, the pop charts gradually, dependably became less amenable to Dylan’s ditties. As if signaling the downturn, Dylan started the decade with consecutive charting singles that peaked just outside the Top 40.

“Wigwam” was the sole single from Dylan’s 1970 album Self Portrait. A loose amble of a song, “Wigwam” can be interpreted as Dylan adamantly refusing to give the audience what they expect. Operating with a reputation as the greatest wordsmith rock ‘n’ roll ever produced? Routinely identified as the lyricist who set the standard for all others to strive for and that no one else can quite reach? Then why not offer a single where the casual, lovely melody is accompanied by nothing but muttered variants of “la la la”?

Dylan made a series of albums with producer Bob Johnston — from Highway 61 Revisited, released in 1965, to New Morning, another 1970 studio effort — and he was ready for a change. Johnston was actually shown the door before New Morning was complete, and Dylan finished the album with Al Kooper, who was a multi-instrumentalist in Dylan’s backing band at the time. In casting around for a new collaborator, Dylan settled on Leon Russell, who’d recently garnered attention for serving as musical director for Joe Cocker and releasing the well-regarded solo album Leon Russell and the Shelter People, which included covers of Dylan’s “A Hard Rain’s a-Gonna Fall” and “It Take a Lot to Laugh, It Takes a Train to Cry.”

At Dylan’s urging, Russell assembled a band of crack musicians who could deliver a raw blues-rock sound. According to drummer Jim Keltner, who was part of that crew, Dylan wrote furiously in the studio, taking fragments of ideas and building them up to suit the chops of the band. Some Dylanologists speculate that the whole process was an attempt to overcome a bout with writer’s block, finding evidence in the opening lines of one of the songs laid down in those sessions, “Watching the River Flow”: “What’s the matter with me/ I don’t have much to say.”

As introduction to Dylan’s change in direction, “Watching the River Flow” was released as a standalone single. Dylan’s label, Columbia Records, emphasized the new approach in advertisements, touting it as “A unique new single from Bob Dylan.” Though not a blockbuster, the song performed just respectably enough that it could reasonably be called a hit. Six months after its release, “Watching the River Flow” led off Bob Dylan’s Greatest Hits Vol. II.

Other entries in this series can be found by clicking on the “Top 40 Smash Near Misses” tag.