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.

In late 1964, Steve Cropper was driving home from his job as the house guitarist at Stax Records, in Memphis, Tennessee, where he was in the midst of working with Otis Redding on his second studio album. Tuned into local radio station WDIA, Cropper heard DJ A. C. “Moohah” Williams introduce one of Redding’s songs by jokingly referring to the soul singer as “Mr. Pitiful.” The newly coined nickname rattled around in Cropper’s head all night, and he had a little tune to go with it by the time he picked up Redding the next morning to commute to the studio for another day’s musical toil. Redding thought it was great, and the two spent the whole drive riffing. They had the song more or less finished by the time they arrived at Stax. They immediately shared the song with the assembled musicians. Cropper later specifically remembered that he taught the bass line to Donald “Duck” Dunn while Redding worked out the horn parts. It was the first song they recorded that time, locked into its finished form within a couple takes. After it was officially released as a single, “Mr. Pitiful” became Redding’s biggest hit on the Billboard Hot 100 to that point, peaking at #41.

In the next couple years, Redding started notching hits. Through 1965, 1966, and 1967, Redding made the Top 40 with seven different singles, though it seemed he could only climb so high. Of that septet, the highest-charting was the first to cross the Top 40 threshold: “I’ve Been Loving You Too Long,” which topped out at #21. Famously, Redding’s biggest hit was the first single released under his name after died tragically in a plane crash en route to a gig at a club called the Factory in Madison, Wisconsin. (The crash into the icy waters of Lake Monona, approximately three miles from the airfield where the plane would have set down, also claimed the lives of four teenaged members of the Bar-Kays, Jimmy King, Ronnie Caldwell, Carl Cunningham, Phalon Jones, as well as pilot Dick Fraser and seventeen-year-old valet Matthew Kelly. Bar-Kays trumpet player Ben Cauley was the lone survivor.) Following the accident, the Stax-associated labels Volt and Atco scrambled to release material from the stockpile of recordings Redding was working in the weeks preceding his death. The first of those posthumous releases was the single “(Sittin’ On) The Dock of the Bay,” a wistful tune Redding co-wrote with Cropper and that was partially inspired by the music being made by the Beatles at the time. It topped the Billboard chart for four weeks in the spring of 1968.

Although nothing that followed came close to the commercial pinnacle of “(Sittin’ On) The Dock of the Bay,” which was quickly cemented as Redding’s signature song, the suddenly iconic performer did become something a chart mainstay for the whole of 1968. The next two Redding singles, “The Happy Song (Dum-Dum)” and “Amen,” also made the Top 40, and one more came extremely close. “I’ve Got Dreams to Remember” is an aching ballad that Redding co-wrote with Joe Rock, basing the lyrics on a pining love poem his wife, Zelda, wrote for him when she was missing him during one of his concert tours. Redding was initially dismissive of Zelda’s words, telling her “You ain’t no songwriter” after her perused the lines. Zelda Redding didn’t even know that her spouse had borrowed from her in huis creative process until after he died and the song was included as the opening track on The Immortal Otis Redding. Still, she got a writing credit on the song, which itself provided a bit of an inheritance. ““Oh yeah,” she told The New York Times earlier this year. “And I get paid.”

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