Teddy Reynolds, blues pianist, songwriter, and singer, was born in Houston on July 12, 1931. He was the son of Ora Lee Reynolds Miles. Reynolds recorded numerous tracks but is most famous among blues aficionados for his studio work and touring with some of the top Texas-based artists of his generation, including Bobby Bland, Texas Johnny Brown, Johnny Copeland, Grady Gaines, Clarence Green, Peppermint Harris (Harrison D. Nelson, Joe "Guitar" Hughes, B. B. King, and Phillip Walker.
Reynolds was raised by his maternal grandmother, Hallie Robinson, in the southeast Houston neighborhood known as the Third Ward. In an interview he reported that his father, also named Theodore, had played piano in "bootleg" houses in Houston. Teddy attended Blackshear Elementary School but discontinued his formal education in the fifth grade. He survived by working a variety of odd jobs until his mid-teens, when his skills on piano, which he had learned at his grandmother's house, earned him a chance to perform in a Third Ward nightclub called Shady's Playhouse (originally Jeff's Playhouse). He soon became a member of the house band there and formed key friendships with guitarists such as Johnny Copeland and Albert Collins, as well as with the man Reynolds always credited as his most significant music teacher, Henry Hayes, plus songwriting collaborator Joe Medwick and pianists Charles Brown and Amos Milburn.
In 1950 Reynolds first recorded in Houston, for the label called Sittin' In With. He provided the vocals for a regional hit single, "Cry Cry Baby," by Ed Wiley and His After Hours Band—and thereafter became known to many as Teddy "Cry Cry" Reynolds. He also released several other singles under his own name from those 1950 sessions, including "Why Baby Why," "Too Late to Change," "Walkin' the Floor Baby," and "Right Will Always Win." In 1958 he recorded for the Mercury label, playing piano on the first disc ("Rock and Roll Lily") ever made by Johnny Copeland, who reciprocated by contributing guitar to Reynolds's several Mercury singles, including "Puppy Dogs."
Reynolds did his most prolific and enduring studio work as a regular session player at Duke-Peacock Records in Houston, which in the 1950s was the largest Black-owned record company in the world. Starting in 1958 and lasting into the mid-1960s, he played piano or organ on classic sides by Bobby Bland and Junior Parker, with whom he toured constantly in a popular twin-bill revue for almost three years.
Throughout the 1960s he maintained residency in California, where he recorded his own singles for the Crown label and backed other artists on projects for various other small labels. During this era he also worked with other Duke–Peacock artists, such as Joe Hinton and Al "TNT" Braggs. In 1970 Reynolds played on the ABC–Dunhill album Together for the First Time, which united Bland with B. B. King.
While living in Los Angeles, he married a woman named Barbara. Apparently they had several children. In late 1970 Reynolds returned from the West Coast with his family to settle permanently in Houston. Sometime after their return, the marriage broke up. He married a second wife, Ester, and worked in the construction and oil-refinery service industries.
In 1986 he began to make music professionally again, joining Grady Gaines's reunited band, the Texas Upsetters. Recording with that group he contributed keyboards, vocals, and several compositions to the CDs Full Gain (1987) and Horn of Plenty (1992), and performed as featured artist on a compilation called Gulf Coast Blues (1990) and various others, all on the Black Top label. In 1991 Reynolds appeared singing and playing piano in a television commercial, so popular that it ran for many years thereafter, for Texas-based Blue Bell Ice Cream. Locally he performed with several groups through the mid-1990s, including the Quality Blues Band, led by his former Duke–Peacock session mate Texas Johnny Brown. Reynolds's final studio work appears on Brown's 1998 CD Nothin' But the Truth. In February 1997 he received an award from the Houston Blues Society. He died in Houston on October 1, 1998.