Frank Sinatra and Willie Nelson, 87, might not seem like a match made in musical heaven, but their friendship goes way back. Ol’ Blue Eyes reportedly called The Red Headed Stranger his favorite singer after hearing his 1978 album Stardust, and the unlikely duo even teamed up for a series of Las Vegas concerts in the ‘80s.
Sinatra died in 1998, but Nelson's admiration has grown only stronger over the years. In 2018 he released My Way, a collection of covers that earned him the Grammy for best traditional pop vocal album, and this month sees the debut of his much-anticipated follow-up That's Life — with 11 newly recorded Sinatra tunes. One was a swingin’ Rat Pack member, the other a honey-voiced outlaw troubadour; so how do their decades-long careers stack up when examined side by side? Here, a by-the-numbers look at two of the towering giants of 20th-century popular music (plus a few choice Willie and Frank videos to enjoy).