Pyle learned his craft by listening to the radio and copying drummers such as Ringo Starr, Buddy Rich, Gene Krupa, and Joe Morello of the Dave Brubeck Quartet. He received his first set of drums when he was approximately the age of 12, a red sparkle Slingerland kit consisting of one bass drum, one rack tom, one floor tom, and a snare drum. He has described his style as “technical.”

After playing with Thickwood Lick in Spartanburg, South Carolina,[citation needed] Pyle joined Lynyrd Skynyrd in 1975. He initially played alongside, and then replaced, original drummer Bob Burns. He made his recording debut in August of that year on “Saturday Night Special”, which became the first single from the band’s third album, Nuthin’ Fancy. In addition to Nuthin’ Fancy, Pyle also played on the albums Gimme Back My Bullets, One More from the Road, Street Survivors, Legend, Southern by the Grace of God and Lynyrd Skynyrd 1991.

He survived the 1977 plane crash that killed lead vocalist and songwriter Ronnie Van Zant, guitarist Steve Gaines, backing vocalist Cassie Gaines, assistant Road Manager Dean Kilpatrick, and the two pilots. Pyle suffered torn chest cartilage but managed to stumble several hundred yards through a creek and a field to a farmhouse to get help. The appearance of Pyle alarmed the 21-year-old farmer Johnny Mote, who mistook him for an escaped convict and fired a warning shot over Pyle’s head.

During his tenure with Lynyrd Skynyrd, he initially played a chrome-plated Jazz Rock Slingerland kit that he had purchased with his Marines discharge check. It featured two rack toms (14 and 15 inches); two floor toms (16 and 18 inches); two bass drums (24 inches); and a Rogers Dynasonic snare drum (14 x 6.5 inches).[citation needed] Later, the Slingerland Drum Company built him a set of blonde-maple drums with red mahogany rims. This kit consisted of four tom-toms up, two toms on the floor, with a double bass drum. He specified no resonant heads on the bottom for better microphone placement, although it made drum-tuning more of a challenge. His cowbell was an actual cowbell.

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