Richardson, who played guitar, began his musical career as a song writer. George Jones later recorded Richardson's "White Lightning", which became Jones' first #1 country hit in 1959 (#73 on the pop charts). Richardson also wrote "Running Bear" for Johnny Preston, his friend from Port Arthur, Texas.

The inspiration for the song came from Richardson's childhood memory of the Sabine River, where he heard stories about Indian tribes. Richardson sang background on "Running Bear", but the recording wasn't released until September 1959, after his death. Within several months it became #1.

The man who launched Richardson as a recording artist was Harold "Pappy" Daily from Houston, Texas. Daily was promotion director for Mercury and Starday Records and signed Richardson to Mercury. Richardson's first single, "Beggar To A King", had a country flavor, but failed to gain any chart action.

He soon cut "Chantilly Lace" as "The Big Bopper" for Pappy Daily's D label. Mercury bought the recording and released it in the summer of 1958. It reached #6 on the pop charts and spent 22 weeks in the national Top 40. It also inspired an answer record by Jayne Mansfield titled "That Makes It".

In "Chantilly Lace", Richardson pretends to have a flirting phone call with his girlfriend; the Mansfield record suggests what his girlfriend might have been saying at the other end of the line. Later that year he scored a second hit, a raucous novelty tune entitled "The Big Bopper's Wedding," in which Richardson pretends to be getting cold feet at the altar.

With the success of "Chantilly Lace," Richardson took time off from KTRM radio and joined Buddy Holly and The Crickets, Ritchie Valens and Dion & the Belmonts for a "Winter Dance Party" tour.

On February 2, 1959, Buddy Holly chartered a Beechcraft Bonanza to take him, Tommy Allsup, and Waylon Jennings to Fargo, North Dakota. Richardson was suffering from the flu and didn't feel comfortable on the group's bus.

Jennings agreed to give up his plane seat to Richardson. Valens had never flown in a small plane and requested Allsup's seat. They flipped a coin, and Valens won the toss.

Early on the morning of February 3, 1959, after a performance at the Surf Ballroom in Clear Lake, Iowa, the small four-passenger Beechcraft Bonanza took off from the Mason City airport during a blinding snow storm. It crashed into Albert Juhl’s corn field several miles after takeoff at 1:05 a.m.

The crash killed all aboard: Buddy Holly, Ritchie Valens, Richardson and the 21-year-old pilot, Roger Peterson. In his 1971 hit song "American Pie," Don McLean referred to this crash as "The Day the Music Died". The name has stayed with it.

Richardson was survived by his wife and 4-year-old daughter. His son, Jay Perry Richardson, was born two months later in April 1959. At the time of his death, Richardson had been building a recording studio in his home in Beaumont, Texas, and was also planning to invest in the ownership of a radio station. He had written 20 new songs he planed to record himself or with other artists.