Following his graduation from Wendell Philips High School in 1909, he entered the world of vaudeville as the partner of singing-comedian Gene Greene. Their act became a tremendous success, leading to a series of recordings with various record companies.

After their team broke up, Straight, together with Roy Bargy (on second piano) and a saxophonist,  formed Straight's Trio aka the Imperial Three, doing unsuccessful recording tests for Victor and Columbia on consecutive days in November 1919. However, a month later the Emerson label released the trio's first records. He also joined the Imperial Player Roll Company as musical director, supervising their entire popular song program as well as being one of their featured artists. At the same time he was musical director for Imperial, he also arranged and performed for rival QRS. In fact, the first ever hand-playedWord Roll issued by QRS was Straight's performance of 'Pretty Baby', released in 1916. He also moonlighted for Wurlitzer-owned label Rolla Artis, using the pseudonym Billie King. Some researchers speculate this may have led to his dismissal from QRS for breach of contract, as his style is readily identifiable.

From 1920, Straight's own orchestra took up most of his time, and although he made rolls for QRS sporadically, his professional life consisted of arranging, performing at the piano and conducting his own orchestra.  He resigned from the Imperial Player Roll Company on January 1, 1922 (just ten days  before QRS bought them out and absorbed them). In 1923, Straight and his new nine-piece band were recording for Paramount, the tracks being simultaneously issued on subsidiary labels as the Frisco Syncopators, Harmograph Dance Orchestra, Manhattan Imperial Orchestra, Broadway Melody Makers and Rendezvous Dance Orchestra. Long resident at the Rainbow Gardens in Chicago, the band was joined by Bix Beiderbecke in 1924.

Joseph "Wingy" Manone also played with Straight, and in 1926, Miff Mole and Wild Bill Davison were on a Brunswick session which produced "Hobo's Prayer"/"Minor Gaff", also issued on Vocalion Records as by the Tennessee Tooters. Most of Straight's 1926-27 sides went out on Brunswick under his own name but some were also issued on Vocalion as the Tuxedo Orchestra. He never worked as a leader after his last Brunswick sessions of August 1928, though he is known to have recorded with the Benson Orchestra of Chicago, run by the agency which handled his own band. They recorded for Paramount and Brunswick. But, his was not a studio orchestra but a working one featured at the top hotels and nightclubs in Chicago.

He remained active as a bandleader until his death in 1940, when he was hit by a speeding car in Chicago. Bookings for Charley Straight's Orchestra were slow during late summer of 1940, and Straight had taken a temporary job as a water sampler for the Sanitary district in Chicago. It was while working over a manhole on the evening of Sunday September 22nd that he was struck and killed by a car driven by one Edward Wehle, a 19 year old residing at 2340
Lincoln Park West. Even though a second job was necessary for Charley Straight, life was not on the wane - he had one of the fullest Fall and Winter bookings
in years. The 'Southeast Economist' newspaper reported: "He was scheduled to appear at numerous South side public and private dances, but, though his spirit will be there, fate has ruled that Charley Straight and his inimitable style will be absent."

Straight's funeral was held on Wednesday September 25th at the Visitation Church. It was large - musicians, song-writers, political figures were amongst those paying their respects.