Over the next five years, Otis put more than a dozen other tunes on the Pop and R&B charts. Among them, "I've Been Loving You Too Long", and "Respect", in 1965 and "Satisfaction" and "Fa Fa Fa Fa Fa" in 1966. He also had hits in 1967 with, "Shake" and "Try A Little Tenderness". Otis was equally expressive with fast and slow songs and his distinctive moving style earned him the nickname, "he Crown Prince Of Soul. He was a tough singer, yet he could handle sentimental ballads with ease. Many of his best records had themes of desperation and lost love, which gave him a second nickname, Mr. Pitiful.
In 1967, Otis became the only Soul singer to show up at the Monterey Pop Festival. He was known to the mostly White, flower-power audience, and came on late, well after mid-night. The crowd was tired and some people were dropping off to sleep when Otis hit the stage just before 1 A.M. Within seconds they were on their feet, worked to a frenzy by his dynamic, exciting sound. Captured on the film and album "Monterey Pop", it was said to be the greatest performance of his life.
Apparently influenced by his new-found hippie friends, Otis came up with a song that matched their easy-going outlook. He wrote it while sitting in a houseboat anchored just off Sausalito, a few miles from San Francisco. It was a soft Pop ballad that began with sea gulls and lapping waves and rocked to a gentle beat. "The Dock Of The Bay" had its own refined tension and expressed the wistful longings of a man alone. The session men who played on the track would later say that the whistling ending came about by accident, when Otis forgot the words to the fade-out scat that he had prepared. The record was cut on December 7th, 1967. Three days later, Otis ended a concert in Madison, Wisconsin and boarded a brand new twin engine Beechcraft to fly to Cleveland. He was very proud of his plane because it showed that after all that time, he had finally begun to make it in the big time. Music magazine, Melody Maker had voted him Top Male Vocalist Of The Year, an honor that they had given to Elvis Presley the previous eight years. It looked like 1968 was going to be his year. The plane took off in heavy fog, and four miles out dropped like a rock into Lake Monona. It sank within seconds, and Otis Redding was killed, along with several members of his band, The Bar-Kays. Only trumpeter Ben Cauley survived the crash.
At his funeral, 4500 people filled the Macon City Auditorium. Joe Tex, Joe Simon, Johnny Taylor, Don Covay, Percy Sledge, Solomon Burke and Sam Moore of Sam And Dave were the pallbearers. He was buried on the ranch he loved so well in Round Oak, thirty miles out of town. Redding was survived by his wife and three children, Otis III, Dexter and Karla.
"Dock Of The Bay" was released in January 1968, and three months later was the number one song in the country. It went on to sell more than four million copies and earn two Grammy Awards for Best R&B Song and Best Male R&B Vocal Performance. The album "The Dock of the Bay" was the first posthumous album to reach the top spot on the UK album chart. Shortly after Redding's death, Atlantic Records, who held the rights to all of Otis' unreleased master recordings, was purchased by Warner Bros. They had enough material for three new studio albums, "The Immortal Otis Redding" (1968), "Love Man" (1969), and "Tell the Truth" (1970), all issued on Atco Records.
In September 2007, Dreams To Remember: The Legacy of Otis Redding, the first official DVD anthology of Redding's live performances, was released by Concord Music Group. The disc featured 16 full-length performances and forty minutes of interviews. On May 18th, 2010, Stax Records released a two-disc collection of Otis Redding's performance at the Whisky a Go Go in April, 1966.