Andrew Wright flew 268kg (591lbs) of the drug from Germany to the UK in eight trips in his light aircraft.
He used his firm, Skyviews R Us Ltd, as a cover for the operation described as "off the scale" by the judge.
Wright, of Toad Hall, Selby, pleaded guilty to conspiracy to import cocaine at the Old Bailey.
The court heard Wright would collect the drugs, which had been bought in Amsterdam by gang member Jamie Williams, from Kassel airport in Hesse, Germany, before flying back to Breighton Airfield in Selby, North Yorkshire.
Having returned to the UK, Williams, 38, would collect the drugs from Wright and deliver them to gang leader, Mark Dowling, 43, in Essex.
The gang used several literary references aside from W E Johns fictional pilot Biggles, including Ginger - his companion - and Skippy
Border control officers smashed the racket in November 2014 when they found four bricks of cocaine in the boot of Wright's Porsche Cayenne and a further 30 hidden in the tail section of his plane.
Wright was paid £1,500 per kilo he imported while "trusted lieutenant" Williams was paid £12,000 plus expenses for his involvement.
Wright's barrister, Tom Gent, said his client became involved in the operation following the death of his wife's son in 2013.
"He lost focus on his business. For many years he and his wife had run a legitimate business in aerial photography. He took his eye off the ball and ran into financial difficulties."
Dowling, of Surman Crescent, in Brentwood, Essex, was jailed for 24 years. Williams, of Romford, Havering, received a 23-year jail term.
Both men had pleaded guilty to their part in the drug smuggling plot between 1 September and 18 November, 2014.
Williams also admitted separate drugs, firearms and money laundering offences.
Mick Maloney, from the National Crime Agency, said: "This crime group ran an organised operation, utilising the piloting skills of Andrew Wright to import large amounts of cocaine.
"With valuable help from our colleagues in the Metropolitan Police, North Yorkshire Police, Border Force and the authorities in Germany we have dismantled a significant criminal enterprise."
A pilot nicknamed Biggles who used his aerial photography business to front a £33.5m cocaine smuggling racket has been jailed for 19 years.