In December 1958, Buddy Holly recorded six original songs on his tape recorder in his New York apartment: Thats What They Say, What To Do, Peggy Sue Got Married, That Makes It Tough, Crying, Waiting, Hoping and Learning The Game. Buddy only taped these songs as a means of recording demos to work on at a later date. Five of these last songs deal with the disappointments of love, mirroring Buddys own misfortunes at the time. He was struggling financially, having to borrow money just to pay his rent and was fighting a legal battle to release royalties owed to him from Norman Petty, his former manager. He had split with The Crickets, in turn losing his childhood friends and his songs were no longer selling well in America, although he was still dominating the British charts. Moving from Texas to New Yorks Greenwich with his new wife, must have also felt very daunting.These problems are echoed in the sadness of these songs and it was due to these financial burdens that he was forced to go back on the road, with the ill fated Winter Dance Party. That Makes It Tough, really highlights Hank Williams influence on Buddy and many believe had he have lived to record the song formally in the studio, it would have been a huge smash for him.