Redding’s breakthrough came in 1958 on disc jockey Hamp Swain’s “The Teenage Party,” a talent contest at the local Roxy and Douglass Theatres. Johnny Jenkins, a locally prominent guitarist, was in the audience and, finding Redding’s backing band lacking in musical skills, offered to accompany him. Redding sang Little Richard’s “Heebie Jeebies.” The combination enabled Redding to win Swain’s talent contest for fifteen consecutive weeks; the cash prize was $5 (US$44 in 2019 dollars). Jenkins later worked as lead guitarist and played with Redding during several later gigs. Redding was soon invited to replace Willie Jones as frontman of Pat T. Cake and the Mighty Panthers, featuring Johnny Jenkins. Redding was then hired by the Upsetters when Little Richard abandoned rock and roll in favor of gospel music. Redding was well paid, making about $25 per gig (US$222 in 2019 dollars), but did not stay long. In mid-1960, Otis moved to Los Angeles with his sister, Deborah, while his wife Zelma and their children stayed in Macon, Georgia. In Los Angeles Redding recorded his first songs, including “Tuff Enuff” written by James McEachin, “She’s All Right,” written with McEachin, and two Redding wrote alone, called “I’m Gettin’ Hip” and “Gamma Lamma” (which he recorded as a single in 1961, under the title “Shout Bamalama”).

At age 18, Redding met 15-year-old Zelma Atwood at “The Teenage Party.” She gave birth to their son Dexter in the summer of 1960 and married Redding in August 1961. In mid-1960, Otis moved to Los Angeles with his sister, Deborah, while Zelma and the children stayed in Macon, Georgia.

When Walden started to look for a record label for Jenkins, Atlantic Records representative Joe Galkin showed interest and around 1962 sent him to the Stax studio in Memphis. Redding drove Jenkins to the session, as the latter did not have a driver’s license. The session with Jenkins, backed by Booker T. & the M.G.’s, was unproductive and ended early; Redding was allowed to perform two songs. The first was “Hey Hey Baby”, which studio chief Jim Stewart thought sounded too much like Little Richard. The second was “These Arms of Mine”, featuring Jenkins on guitar and Steve Cropper on piano. Stewart later praised Redding’s performance, saying, “Everybody was fixin’ to go home, but Joe Galkin insisted we give Otis a listen. There was something different about [the ballad]. He really poured his soul into it.” Stewart signed Redding and released “These Arms of Mine”, with “Hey Hey Baby” on the B-side. The single was released by Volt in October 1962 and charted in March the following year. It became one of his most successful songs, selling more than 800,000 copies.

“These Arms of Mine” and other songs from the 1962–1963 sessions were included on Redding’s debut album, Pain in My Heart. “That’s What My Heart Needs” and “Mary’s Little Lamb” were recorded in June 1963. The latter is the only Redding track with both background singing and brass. It became his worst-selling single. The title track, recorded in September 1963, sparked copyright issues, as it sounded like Irma Thomas’s “Ruler of My Heart”. Despite this, Pain in My Heart was released on March 1964, with the single peaking at number 11 on the R&B chart, number 61 on the Billboard Hot 100, and the album at number 103 on the Billboard 200.

In November 1963, Redding, accompanied by his brother Rodgers and an associate, former boxer Sylvester Huckaby (a childhood friend of Redding’s), traveled to New York to perform at the Apollo Theater for the recording of a live album for Atlantic Records. Redding and his band were paid $400 per week (US$3,340 in 2019 dollars) but had to pay $450 (US$3,758 in 2019 dollars) for sheet music for the house band, led by King Curtis, which left them in financial difficulty. The trio asked Walden for money. Huckaby’s description of their circumstances living in the “big old raggedy” Hotel Theresa is quoted by Peter Guralnick in his book Sweet Soul Music. He noted meeting Muhammad Ali and other celebrities. Ben E. King, who was the headliner at the Apollo when Redding performed there, gave him $100 (US$835 in 2019 dollars) when he learned about Redding’s financial situation. The resulting album featured King, the Coasters, Doris Troy, Rufus Thomas, the Falcons and Redding. Around this time Walden and Rodgers were drafted by the army; Walden’s younger brother Alan joined Redding on tour, while Earl “Speedo” Simms replaced Rodgers as Redding’s road manager.

Most of Redding’s songs after “Security”, from his first album, had a slow tempo. Disc jockey A. C. Moohah Williams accordingly labeled him “Mr. Pitiful”, and subsequently, Cropper and Redding wrote the eponymous song. That and top 100 singles ” Chained and Bound”, “Come to Me” and “That’s How Strong My Love Is” were included on Redding’s second studio album, The Great Otis Redding Sings Soul Ballads, released in March 1965. Jenkins began working independently from the group out of fear Galkin, Walden and Cropper would plagiarize his playing style, and so Cropper became Redding’s leading guitarist. Around 1965, Redding co-wrote “I’ve Been Loving You Too Long” with Jerry Butler, the former lead singer of the Impressions. That summer, Redding and the studio crew arranged new songs for his next album. Ten of the eleven songs were recorded in a 24-hour period on July 9 and 10 in Memphis. Two songs, “Ole Man Trouble” and “Respect”, had been finished earlier, during the Otis Blue session. “Respect” and “I’ve Been Loving You” were later recut in stereo. The album, entitled Otis Blue: Otis Redding Sings Soul, was released in September 1965. Otis Blue also includes Redding’s much-loved cover of “A Change Is Gonna Come” in 1965.

In late 1966, Redding returned to the Stax studio and recorded several tracks, including “Try a Little Tenderness”, written by Jimmy Campbell, Reg Connelly and Harry M. Woods in 1932. This song had previously been covered by Bing Crosby and Frank Sinatra, and the publishers unsuccessfully tried to stop Redding from recording the song from a “negro perspective”. Today often considered his signature song, Jim Stewart reckoned, “If there’s one song, one performance that really sort of sums up Otis and what he’s about, it’s ‘Try a Little Tenderness’. That one performance is so special and so unique that it expresses who he is.” On this version Redding was backed by Booker T. & the M.G.’s, while staff producer Isaac Hayes worked on the arrangement. “Try a Little Tenderness” was included on his next album, Complete & Unbelievable: The Otis Redding Dictionary of Soul. The song and the album were critically and commercially successful—the former peaked at number 25 on the Billboard Hot 100 chart and at number 4 on the R&B chart.

The spring of 1966 marked the first time that Stax booked concerts for its artists. The majority of the group arrived in London on March 13, but Redding had flown in days earlier for interviews, such as at “The Eamonn Andrews Show”. When the crew arrived in London, the Beatles sent a limousine to pick them up. Booking agent Bill Graham proposed that Redding play at the Fillmore Auditorium in late 1966. The gig was commercially and critically successful, paying Redding around $800 to $1000 (US$7,880 in 2019 dollars) a night. It prompted Graham to remark afterward, “That was the best gig I ever put on in my entire life.” Redding began touring Europe six months later.

Shortly after Redding’s death, Atlantic Records, distributor of the Stax/Volt releases, was purchased by Warner Bros. Stax was required to renegotiate its distribution deal and was surprised to learn that Atlantic actually owned the entire Stax/Volt catalog. Stax was unable to regain the rights to its recordings and severed its Atlantic relationship. Atlantic also held the rights to all unreleased Otis Redding masters. It had enough material for three studio albums—The Immortal Otis Redding (1968), Love Man (1969), and Tell the Truth (1970)—all issued on its Atco Records label. A number of successful singles emerged from these LPs, among them “Amen” (1968), “Hard to Handle” (1968), “I’ve Got Dreams to Remember” (1968), “Love Man” (1969), and “Look at That Girl” (1969). Singles were also lifted from two live Atlantic-issued Redding albums, In Person at the Whisky a Go Go, recorded in 1966 and issued in 1968 on Atco, and Historic Performances Recorded At The Monterey International Pop Festival, a Reprise Records release featuring some of the live performances at the festival by the Jimi Hendrix Experience on side one and Redding on side two.

In March 1967, Stax released King & Queen, an album of duets between Redding and Carla Thomas, which became a certified gold record. It was Jim Stewart’s idea to produce a duet album, as he expected that “[Redding’s] rawness and [Thomas’s] sophistication would work”. The album was recorded in January 1967, while Thomas was earning her M.A. in English at Howard University. Six out of ten songs were cut during their joint session; the rest were overdubbed by Redding in the days following, because of his concert obligations. Three singles were lifted from the album: “Tramp” was released in April, followed by “Knock on Wood” and “Lovey Dovey”. All three reached at least the top 60 on both the R&B and Pop charts. The album charted at number 5 and 36 on the Billboard Pop and R&B charts, respectively.

In 1967, Redding performed at the influential Monterey Pop Festival as the closing act on Saturday night, the second day of the festival. He was invited through the efforts of promoter Jerry Wexler. Until that point, Redding was still performing mainly for black audiences. At the time, he “had not been considered a commercially viable player in the mainstream white American market.” But after delivering one of the most electric performances of the night, and having been the act to most involve the audience, “his performance at Monterey Pop was therefore a natural progression from local to national acclaim,…the decisive turning-point in Otis Redding’s career.” His act included his own song “Respect” and a version of the Rolling Stones’ “Satisfaction.” Redding and his backing band (Booker T. & the M.G.’s with the Mar-Keys horn section) opened with Cooke’s “Shake”, after which he delivered an impulsive speech, asking the audience if they were the “love crowd” and looking for a big response. The ballad “I’ve Been Loving You” followed. The last song was “Try a Little Tenderness”, including an additional chorus. “I got to go, y’all, I don’t wanna go”, said Redding and left the stage of his last major concert. According to Booker T. Jones, “I think we did one of our best shows, Otis and the MG’s. That we were included in that was also something of a phenomenon. That we were there? With those people? They were accepting us and that was one of the things that really moved Otis. He was happy to be included and it brought him a new audience. It was greatly expanded in Monterey.” According to Sweet Soul Music, musicians such as Brian Jones and Jimi Hendrix were captivated by his performance; Robert Christgau wrote in Esquire, “The Love Crowd screamed one’s mind to the heavens.”

Before Monterey, Redding wanted to record with Conley, but Stax was against the idea. The two moved from Memphis to Macon to continue writing. The result was “Sweet Soul Music” (based on Cooke’s “Yeah Man”), which peaked at number 2 on the Billboard Hot 100. By that time, Redding had developed polyps on his larynx, which he tried to treat with tea and lemon or honey. He was hospitalized in September 1967 at Mount Sinai Hospital in New York to undergo surgery.

Redding’s music made him wealthy. According to several advertisements, he had around 200 suits and 400 pairs of shoes, and he earned about $35,000 per week for his concerts. He spent about $125,000 in the “Big O Ranch.” As the owner of Otis Redding Enterprises, his performances, music publishing ventures and royalties from record sales earned him more than a million dollars in 1967 alone. That year, one columnist said, “he sold more records than Frank Sinatra and Dean Martin combined.” After the release of Otis Blue, Redding became a “catalogue” artist, meaning his albums were not immediate blockbusters, but rather sold steadily over time.

By 1967, the band was traveling to performances in Redding’s Beechcraft H18 airplane. On December 9, they appeared on the Upbeat television show produced in Cleveland. They played three concerts in two nights at a club called Leo’s Casino. After a phone call with his wife and children, Redding’s next stop was Madison, Wisconsin; the next day, Sunday, December 10, they were to play at the Factory nightclub, near the University of Wisconsin.

“(Sittin’ On) The Dock of the Bay” was released in January 1968. It became Redding’s only single to reach number one on the Billboard Hot 100 and the first posthumous number-one single in U.S. chart history. It sold approximately four million copies worldwide and received more than eight million airplays. The album The Dock of the Bay was the first posthumous album to reach the top spot on the UK Albums Chart.

After Redding’s death, France’s Académie du Jazz (Academy of Jazz) named an award after him. The Prix Otis Redding is given to the best record release in the field of R&B. Redding was the first recipient of the award for The Otis Redding Story on Stax; following winners of the award include Aretha Franklin, Ike & Tina Turner, and Curtis Mayfield. In 1968, the National Association of Television and Radio Announcers (NATRA) created the Otis Redding Award in his honor.

Redding posthumously won two Grammy Awards for “(Sittin’ On) The Dock of the Bay” at the 11th Annual Grammy Awards in 1969. The Rock and Roll Hall of Fame inducted Redding in 1989, declaring his name to be “synonymous with the term soul music that arose out of the black experience in America through the transmutation of gospel and rhythm and blues into a form of funky, secular testifying.” In 1988, he was inducted into the Georgia Music Hall of Fame. Five years later, the United States Post Office issued a 29-cent commemorative postage stamp in his honor. Redding was inducted into the Songwriters Hall of Fame in 1994, and in 1999 he received the Grammy Lifetime Achievement Award. The Rock and Roll Hall of Fame included three Redding recordings, “Shake”, “(Sittin’ On) The Dock of the Bay”, and “Try a Little Tenderness”, on its list of “The 500 Songs That Shaped Rock and Roll”.

Redding’s body was recovered the next day when the lake was searched. The family postponed the funeral from December 15 to 18 so that more could attend, and the service took place at the City Auditorium in Macon. More than 4,500 people came to the funeral, overflowing the 3,000-seat hall. Johnny Jenkins and Isaac Hayes did not attend, fearing their reaction would be worse than Zelma Redding’s. Redding was entombed at his ranch in Round Oak, about twenty miles (30 km) north of Macon. Jerry Wexler delivered the eulogy. Redding died just three days after re-recording “(Sittin’ On) The Dock of the Bay,” and was survived by Zelma and four children, Otis III, Dexter, Demetria, and Karla. On November 8, 1997, a memorial plaque was placed on the lakeside deck of the Madison convention center, Monona Terrace.

In 2002, the city of Macon honored its native son by unveiling a memorial statue (32°50′19.05″N 83°37′17.30″W / 32.8386250°N 83.6214722°W / 32.8386250; -83.6214722) in the city’s Gateway Park. The park is next to the Otis Redding Memorial Bridge, which crosses the Ocmulgee River. The Rhythm and Blues Foundation named Redding as the recipient of its 2006 Pioneer Award. Billboard awarded Redding the “Otis Redding Excellence Award” the same year. A year later he was inducted into the Hollywood’s Rockwalk in California.

In September 2007, the first official DVD anthology of Redding’s live performances was released by Concord Music Group, then owners of the Stax catalog. Dreams to Remember: The Legacy of Otis Redding featured 16 full-length performances and 40 minutes of new interviews documenting his life and career. On May 18, 2010, Stax Records released a two-disc recording of three complete sets from his Whisky a Go Go date in April 1966. All seven sets from his three-day residency at the venue were released as Live at the Whisky a Go Go: The Complete Recordings in 2016, a 6-CD box set that won a Grammy Award for Best Album Notes.

On August 17, 2013, in Cleveland, Ohio, the city where he did his last show at Leo’s Casino, Redding was inducted into the inaugural class of the Rhythm & Blues Music Hall of Fame at Cleveland State University.