Wakeman was born on 18 May 1949 in the west London suburb of Perivale. The only child of Cyril Frank Wakeman and Mildred Helen Wakeman, the three lived in Wood End Gardens in nearby Northolt. Cyril played the piano in a dance band while he was in the army and worked at a building suppliers, joining as an office boy at fourteen to become one of its directors. Mildred worked at a removals firm. Wakeman attended Drayton Manor Grammar School in Hanwell, in 1959. The family spent their summer holidays in Exmouth.
When Wakeman turned seven, his father paid for weekly piano lessons with Dorothy Symes which lasted for eleven years. She recalled that Wakeman "passed everything with a distinction" and was an "enjoyable pupil to teach, full of fun and with a good sense of humour", but noted his lack of self-discipline when it came to practising. In 1960, Symes entered Wakeman in his first music competition and he went on to win many awards, certificates, and cups in contests held around London. Wakeman then took up the clarinet at age twelve and in his teenage years, attended church and learned the church organ, became a Sunday school teacher, and chose to be baptised at eighteen.
Wakeman described himself at school as "a horror ... I worked hard in the first year, then eased up". In 1961, during his time at Drayton Manor school, Wakeman played in his first band, the trad jazz outfit Brother Wakeman and the Clergymen, with a uniform of the school shirt put on the wrong way round. In 1963, at fourteen, Wakeman joined the Atlantic Blues, a local blues group that secured a year's residency at a mental health rehabilitation club in Neasden. Two years later, Wakeman passed his O Levels in English, maths, art and music, and went on to study music, art, and British constitution at A-level. In 1966, he joined the Concordes, later known as the Concorde Quartet, playing dance and pop songs at local events with his cousin Alan Wakeman on saxophone and clarinet. Wakeman used the money earned from their gigs to buy a Pianet, his first electronic instrument.
That year he also formed a dance band called the Green Dolphin Trio, spending a year's residency at a social club in Alperton, and Curdled Milk, a joke on "Strange Brew" by Cream, to play at the annual school dance. The band were unpaid after Wakeman lost control of his car and drove across the headmaster's rose garden at the front of the school, thereby forfeiting their performance fee to pay for the damage. In 1967, Wakeman began a tenure with the Ronnie Smith Band, a dance group based at the Top Rank ballroom in Watford. He was sacked in the following year after not taking the dance music seriously enough, but was reinstated and performed in Reading. It was there where he met their singer Ashley Holt, who later sang on many of Wakeman's future albums and tours.
In 1968, Wakeman secured a place at the Royal College of Music in London, studying the piano, clarinet, orchestration, and modern music, with the intention of becoming a concert pianist. To enter he needed to pass eight music exams to earn his A-level in the subject, which required him, as his mother remembered, "to do two years' work in ten months". Wakeman put in the effort following a ten shilling bet with his music teacher who believed he would not succeed, and refusing his father's offer to work with him. Wakeman joined the Royal College on a performers course before a change to the teachers course, but quickly found out that "everyone else there was at least as good as me; and a lot of them much better." He adopted a more relaxed attitude to his studies, spending much of his time drinking in pubs and with the staff at the Musical Bargain Centre, a music shop in Ealing.
Wakeman's first booking as a session musician, and his first time in a recording studio, occurred when guitarist Chas Cronk entered the shop one morning in need of an organist and brass arranger for members of the Ike & Tina Turner band. During the session Wakeman met producers Tony Visconti, Gus Dudgeon, and Denny Cordell Cordell was impressed with his performance and offered him more session work for artists at Regal Zonophone Records, which Wakeman accepted and he began skipping college in favour of sessions.