Charlton is related to several professional footballers on his mother's side of the family: his uncles were Jack Milburn (Leeds United and Bradford City), George Milburn (Leeds United and Chesterfield), Jim Milburn (Leeds United and Bradford City) and Stan Milburn (Chesterfield, Leicester City and Rochdale), and legendary Newcastle United and England footballer Jackie Milburn, was his mother's cousin. However, Charlton credits much of the early development of his career to his grandfather Tanner and his mother Cissie. His elder brother, Jack, initially worked as a miner before applying to the police, only to also become a professional footballer with Leeds United. His other brother, Tommy, plays walking football for the Mature Millers club in Rotherham.

On 9 February 1953, then a Bedlington Grammar School pupil, Charlton was spotted playing for East Northumberland schools by Manchester United chief scout Joe Armstrong. Charlton went on to play for England Schoolboys and the 15-year-old signed with United on 1 January 1953, along with Wilf McGuinness, also aged 15. Initially his mother was reluctant to let him commit to an insecure football career, so he began an apprenticeship as an electrical engineer; however, he went on to turn professional in October 1954.  Charlton became one of the famed Busby Babes, the collection of talented footballers who emerged through the system at Old Trafford in the 1940s, 1950s and 1960s as Matt Busby set about a long-term plan of rebuilding the club after the Second World War. He worked his way through the pecking order of teams, scoring regularly for the youth and reserve sides before he was handed his first team debut against Charlton Athletic in October 1956. At the same time, he was doing his National service with the Royal Army Ordnance Corps in Shrewsbury, where Busby had advised him to apply as it meant he could still play for Manchester United at the weekend. Also doing his army service in Shrewsbury at the same time was his United teammate Duncan Edwards.  Charlton played 14 times for United in that first season, scoring twice on his debut and managing a total of 12 goals in all competitions, and including a hat-trick in a 5-1 away win over Charlton Athletic in the February. United won the league championship but were denied the 20th century's first "double" when they controversially lost the 1957 FA Cup Final to Aston Villa. Charlton, still only 19, was selected for the game, which saw United goalkeeper Ray Wood carried off with a broken cheekbone after a clash with Villa centre forward Peter McParland. Though Charlton was a candidate to go in goal to replace Wood (in the days before substitutes, and certainly before goalkeeping substitutes), it was teammate Jackie Blanchflower who ended up between the posts.  Charlton was an established player by the time the next season was fully underway, which saw United, as current League champions, become the first English team to compete in the European Cup. Previously, the Football Association had scorned the competition, but United made progress, reaching the semi-finals where they lost to holders Real Madrid. Their reputation was further enhanced the next season as they reached the quarter finals to play Red Star Belgrade. In the first leg at home, United won 2-1. The return in Yugoslavia saw Charlton score twice as United stormed 3-0 ahead, although the hosts came back to earn a 3-3 draw. However, United maintained their aggregate lead to reach the last four and were in jubilant mood as they left to catch their flight home, thinking of an important League game against Wolves at the weekend.

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