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San Francisco's Tim Flannery can usually be found doing one of two things: flashing a sign or singing a song

Giants third base coach Tim Flannery learned most of his baseball history from song lyrics, and he doesn't hesitate to use those lyrics to teach. Not long ago he shared a cautionary tale from the work of Chuck Brodsky, whose 2002 album The Baseball Ballads includes the story of Fred (Bonehead) Merkle, who cost the 1908 Giants a chance to win the pennant when as a base runner he failed to tag second base on what would have been a walk-off single. "They thought it was a bedtime story," says Flannery. "But it could happen again."

Yet baseball is rarely the overt subject of the songs written by Flannery, a guitarist and singer-songwriter whose bluegrass style reflects influences that range from the Kentucky roots of his banjo-playing grandmother to the country rock of the late Gram Parsons. "A lot of my songs could be baseball songs, even though they aren't about bats and balls," he says. "They are about being on the road, and the characters you meet out on the road."

After his 11-year career as an infielder with the Padres ended in 1989, Flannery, 53, managed for several years in the minors, often pulling out his guitar and harmonica for the 15-hour bus rides. "The guitar was a great way to connect with the players when I was managing," says Flannery, who plays 20-plus gigs every off-season and has performed with Willie Nelson, Jackson Browne and Jimmy Buffett. Now, though, he says, "Baseball holds your music back. I don't want baseball fans to show up thinking I'm going to do baseball songs. Our following is music people. I have two separate lives." Some people find that weird, he adds. "They ask, 'Why do you play music?' That's like someone asking me, 'Do you want water or air?' I have to have both."

Like Tim Flannery, a number of musicians have made the transition from professional athlete to musician. Here are our fave five.

Carlos Arroyo

The 10-year NBA veteran launched his own label, and his 2010 reggaeton single, "Se Va Conmigo," established him as a player to watch on the urban Latin music scene.

Joe Frazier

Smokin' Joe started out as a singer, working nightclubs when he wasn't boxing on the weekends. He sang throughout his career, and his 1976 single "If You Go, Stay Gone," has a nice, soulful vibe.

Mike Reid

It's hard to believe that the former trench warrior and All-Pro on the Bengals' defensive line wrote Bonnie Raitt's achingly beautiful "I Can't Make You Love Me," but he did.

Wayman Tisdale

A star at Oklahoma and a 12-year NBA vet, Tisdale, who died in 2009, laid down smooth-jazz bass lines on eight albums. Face to Face, in 2001, hit No. 1 on the Billboard contemporary jazz chart.

Bernie Williams

He's played centerfield at Yankee Stadium and classical guitar concerts around the country—the man knows big stages. His 2009 album Moving Forward was nominated for a Latin Grammy.