In 1908, he toured alongside M. M. Thiese's (Mortimer M. Thiese) Rollickers burlesque show. Unlike today, burlesque of the time was a form of rowdy, fast-paced variety entertainment typically consisting of comedy sketches, musical numbers and short comedy plays. Thiese had previously worked with Henry Pincus to stage The Maid and the Millionaire. Thiese was known for an energetic approach to the stage and managed several touring companies across the "Western Burlesque Wheel". This was a large, organised circuit of theatres which was used to map out exactly which cities a travelling burlesque troupe would visit. Morton's performances with The Rollickers elevated his visibility after leaving the police force and allowed him to become a headline attraction on the prestigious circuits managed by Benjamin Franklin Keith and Sylvester Z. Poli. Morton toured with these as a "single", meaning an individual solo performer who would travel alone without a troupe. Until his retirement in 1928, he spent significant amounts of time travelling as required by the United Booking Office. As he was prominent on the B. F. Keith circuit, he was forced to adapt to Keith's rigid rules. Keith was known to hand out "blue envelopes" to performers (Morton included) which contained orders to censor their acts, resulting in a lot of Morton's rough and more suggestive humour had to be stripped to satisfy Keith's family-friendly mandates. 

This lifestyle was typically very difficult for the artist. Morton lived out of his trunk or from boarding houses, and he would often turn up at the theatre on Monday morning, conduct sound checks to see if his voice projected well, and would then perform up to four continuous shows a day. Trade publications at the time would track his movements as he travelled between competing syndicates, and he became known as a dependable crowd pleaser. 

Morton's performing life was closely interwoven with his recording life, as many of his circuits brought him through the places where the dominant record labels' studios were based (Columbia in New York City, Victor in Camden, New Jersey and Edison out of Orange, New Jersey). He would book session days during his downtime, typically when he was given a week gap between theatre contracts. Morton was known to record songs which he had already performed live on stage dozens of times to save being forced to re-do a master disc by making a mistake or missing a note. This meant he could avoid having to spend days recording a single song, and could instead produce multiple in a single session at a standard which was compared to his on-stage persona. 

He entered the recording industry at a pivotal moment when the market was still transitioning between wax cylinders and flat shellac discs. He tried to reach all households, recording on both the flat discs and four-minute wax cylinders such as "A Singer Sang a Song" (which he recorded in 1908) and durable celluloid cylinders for the Indestructible Record Company. By 1911, Morton's reputation had evolved, and sheet music publishers realised that if he sang a song, people would buy the sheet music to play at home. Because of this, publishers in Tin Pan Alley were known to push their new songs onto Morton. It was around the same time he recorded "The Oceana Roll" which became one of the definitive hits of the decade, and was pressed as the B-side of Collins and Harlan's rendition of "Alexander's Ragtime Band", making it a part of one of the highest-selling double sided releases of the pre-Great War era. 

He continued recording up until 1917, recording two songs for Emerson Records (which was, at that time, a newly formed label known for making small, budget-friendly discs). These songs were "Come Out of the Kitchen Mary Ann" and "Just a Little Bit of Monkey Left in You and Me".