In court documents filed last week, Cessna, an aviation company based in Wichita, Kan., sued Holland for not fully paying for one of the planes he purchased through the company when he bought it years ago.

Holland's company, Jet Racers, Inc., currently owes the amount due under the Promissory Note, which, as of April 21, 2014, totals $782,422.43 and includes principal in the amount of $734,794.43, interest in the amount of $31,887.04, late fees in the amount of $15,740.69 with daily interest accruing at a rate of $80.32.

Unable to make the payments on his third and newest plane, a Cessna, Holland received authorization from the manufacturer to put the aircraft up for sale and offered up his two others, a Czech made Aero Vodochody and a Texas built Mooney M20R, as collateral. Selling the Cessna for less than he owed, Holland signed a new loan for the two remaining planes and the unpaid balance of the Cessna. The singer was to pay 71 monthly payments of $8,726.00 with one final balloon payment of $395,244.26.