Pain in My Heart, recorded in September 1963, sounded like Irma Thomas' Ruler of My Heart, sparked copyright issues but still peaked at number 20 on the Billboard Hot 100. Further chart action came in the form of Mr. Pitiful, Chained And Bound, and That's How Strong My Love Is all of which turned up on Redding's second album, The Great Otis Redding Sings Soul Ballads, released in March 1965. A third album, Otis Blue: Otis Redding Sings Soul appeared six months later.
While he still wasn’t a household name as far as the wider community was concerned, Otis was doing well enough to be able to pay $125,000 for a 300-acre ranch in Georgia (the Big O Ranch). It was, according to Gerri Hirshey's Nowhere to Run: The Story of Soul Music, the land near Macon that his ancestors had been slaves on. In league with manager Walden operated a couple of production companies, grooming proteges including Arthur Conley, the Sweet Soul Music man.
Things started to move up a gear when Redding performed at the Whisky a Go Go on the Los Angeles’ Sunset Strip, and as one of the first soul artists to perform on the West Coast he picked up positive reviews in the press and the Northern spring of 1966 saw the Stax Volt tour of Europe, with Redding headlining a revue that reached substantial new audiences. Back in the States late 1966 saw him back on the West Coast, playing Bill Graham’ Fillmore Auditorium for around $800 to $1000 a night. In between, The Soul Album and Complete & Unbelievable: The Otis Redding Dictionary of Soul appeared under his own name and there was further chart action in the form of the gold record-winning King & Queen, cut in January 1967 with Carla Thomas, daughter of Rufus, who was studying for an M.A. in English at Howard University.
A stint back in Europe at the Paris Olympia with other performances in London and Stockholm resulted in Otis Redding: Live in Europe, but his appearance to close out the Saturday night show at the Monterey Pop Festival was as things turned out, his last major concert.