That Makes It Tough, was recorded in December of 1959, on what has become known as The Apartment Tapes. On these tapes, (which were left behind in Buddy’s New York Apartment after his passing), we find a more sophisticated Buddy Holly, a man with a new found direction, and a brand new beginning. But as history reminds us, it was never meant to be.

On a frigid February night in 1959, a small twin-engine plane carrying Buddy Holly, the Big Bopper, and Ritchie Valens crashed into a Clearlake Iowa cornfield, immortalizing forever in time, "The Day the Music Died'. But as it turned out, Buddy Holly had left behind a few songs that he had recorded (with just vocals and acoustic guitar) on an Ampex Tape Recorder, in the Apartment he shared with his wife Maria Elena in New York City. Maria Elena later gave the tapes to Mr. and Mrs. Holley, who in turn had entrusted them to Norman Petty, Buddy’s Producer and Manager.

By December 1958, Buddy Holly had been through a lot. He’d had a falling-out with the Crickets, who decided to stay in Texas and do their own thing after Holly relocated to New York. Wanting to broaden his horizons, Buddy fired Norman Petty as his Producer and Manager. Shortly thereafter, legal and financial entanglements ensued. Many blame these developments for Buddy’s decision to participate in February’s ill-fated Winter Dance Party Tour. It was during these times, that Buddy wrote "That Makes It Tough".

This is how the Story goes.

On August 15, 1958, Maria Elena and Buddy were wed at the home of Buddy’s parents, in a simple ceremony performed by Buddy's minister. After their honeymoon, Buddy and Maria Elena moved to The Brevoort Apartments on 8th Street, in New York. The Apartment was near New York City's fabled Greenwich Village. Buddy felt that remaining in the city was best for his career. Although he continued to perform and record with The Crickets, their relationship had begun to change. The group no longer traveled together. Buddy became displeased by the group's behavior. The Crickets admitted they were "a bit out of hand". Meanwhile, Buddy’s relationship with Norman Petty had become even more strained. Norman was not happy with Buddy's marriage. He feared that it would cause Buddy to lose his female fans.  Norman suggested that Maria Elena be known as the group's secretary. As September and October passed, their relationship only worsened. Finally, in mid-October, Buddy and the Crickets decided to terminate their association with Norman Petty. Jerry Allison and J.B. Maudlin arrived back in Lubbock, several days before Buddy. After a chance meeting with Norman Petty, Jerry and J.B. were persuaded to continue working with Norman. The Crickets had decided to let Buddy go solo. Buddy also wanted his Independence. He told The Crickets they were welcome to rejoin him if they changed their minds. He was not happy with the turn of events...but Buddy was confident that his decision was a right one. He and Maria Elena returned to New York. 

His plan was to be, 'No more tours until the turn of the new year". Far from being idle, Buddy continued to write and record. He was full of ideas and plans for the future. In late January, Buddy began a General Artists' Corporation Tour, "The Biggest Show of the Stars of 1959." He asked Waylon Jennings, Tommy Allsup and drummer Charles Bunch to accompany him on the tour. Maria Elena was expecting their first child, so she did not join Buddy on the tour. (Later, she tragically lost the baby to a miscarriage). The show included Ritchie Valens, the 17-year old Mexican-American whose song "Donna" was the nation's biggest hit, J.P. (The Big Bopper) Richardson, a 27-year-old ex-Texas D.J., whose "Chantilly Lace" was a top of the chart contender, and Dion and the Belmonts. The entire group traveled by bus under conditions far from being comfortable. On Monday, February 2, the show played in Clear Lake Iowa. Buddy chartered a small plane for himself, Tommy Allsup and Waylon Jennings instead of riding the bus to the next stop in Moorehead Minnesota. They hoped to arrive early enough to have their suits cleaned. Plans were changed at the last minute when J.P. Richardson and Ritchie Valens took Jennings and Allsup's places. Tommy Allsup remembers: "I was the one who chartered the plane, but I flipped a coin with Ritchie Valens - he kept bugging me all night that he'd never flown in a little plane. He won the toss." When the Big Bopper came down with the flu, Waylon gave his seat to him. A Tragic irony touched Buddy Holly's death. On the night of the crash, both Jerry Allison and J.B. Mauldin were trying to reach Buddy, in hopes that they would get back together as a group.

Fast Forward to August, 11th. 2002

From Slow Burning Ashes to a New Phoenix Rising, Buddy Holly’s music still lives on in the Steve Richards remake of one of Buddy Holly’s last known songs from the Apartment Tapes. "That Makes it Tough" was written during a time of great change for Buddy. He was moving away from his traditional Signature Sound, to a more sophisticated, experimental blues dynamic. With Maria Elena’s encouragement, Steve has gathered a crossroad of musicians including bassist Dave Ellefson and lead guitarist Marty Friedman of Megadeth fame along with his Nashville friends keyboardist Jimmy Nichols and pedal steel guitarist Mike G. Smith to record "That Makes It Tough". Maria Elena, says, "I felt that song, whoever records it, would probably have a hit on their hands, because it's a great song. When I heard (Steve) sing, I knew it would be perfect for him." It was Steve’s wife Victoria who came up with the idea of encompassing Buddy’s entire career into "That Makes It Tough" by combining Country, (his early Nashville days) with Rock, (to which we all know of Buddy), and Blues (the direction he was heading with the Apartment Tapes) into the final track. We believe we’ve been able to accomplished just that. It’s truly a great honor to be able to record "That Makes It Tough" Marty Friedman said it best, "It’s almost like he’s rising from the dead, It’s my connection to the Legend". How True Marty, How True"..

See Article by Music Industry News Network: Multi-talented Singer/Songwriter Steve Richards Teams With Former Megadeth Members To Record Buddy Holly Song