LOS ANGELES, CA - FEBRUARY 08:  Musician Paul McCartney performs during the 51st Annual Grammy Awards held at the Staples Cen
Kevin Winter

Paul McCartney has spent 50 of his 69 years making sweet, sweet music and he's not ready to call it quits yet. Just this week he released a new album of jazz-pop standards (for a taste of Kisses on the Bottom, you can stream Paul’s in-studio live performance Thursday night).

Even if his new album skews toward the old-timey, Macca is anything but past his prime. We decided to take a look at some of his songs that challenge the notion of McCartney as the “cute Beatle." Here are 20 songs released since Paul passed the 50 year mark that show he's making some of the most risky, vital, and hard-rocking music of his career.

20. "Big Boys Bickering": This environmental protest song finds the typically polite Paul using the F-word… seven times! Don’t mess with Mother Nature’s Son, apparently. [Off the Ground: The Complete Works, 1993]

19. “My Valentine”: Backed by Diana Krall’s jazz band and assisted by Clapton, McCartney crafted this original song for his latest covers-heavy album. It’s a melancholy ballad that Chet Baker would have been happy to have been sad enough to sing. [Kisses on the Bottom, 2012]

18. “It’s So Easy”: Covering his teenage hero Buddy Holly, Macca hoots and hollers on this barnstorming cover like he’s lost his mind… or maybe just his dentures. [Appears on Rave On Buddy Holly compilation, 2011]

17. "Free Now": Using unreleased studio chatter from the Beatles and employing the Super Furry Animals as his helper monkeys, McCartney released an experimental album of patched-together electronica, reminding us he takes far more risks than his detractors give him credit for. [Liverpool Sound Collage, 2000]

16. "Riding Into Jaipur": Recorded around the time George Harrison was dying, it seems likely that this gentle Eastern-inflected tune was Paul's tribute to his departing mate. [Driving Rain, 2001]

15. "Try Not to Cry": One of two rock 'n' roll throwbacks he wrote after Linda passed. McCartney obliquely addressed loss and trying to move on with this Chuck Berry-styled staccato rocker. [Run Devil Run, 1999]  

14. "Beautiful Night": An addictive truffle with a raucous sing-a-long second act—yep, that's Ringo chiming in at the end. [Flaming Pie, 1997]

13. "Only Mama Knows”: Sounding like a sequel to “Live and Let Die,” this savage rocker about a baby found in an airport (transcontinental Moses?) showcases latter-day McCartney at his best: freewheeling, sly and effortless. [Memory Almost Full, 2007] 

12. "Rinse the Raindrops": Try on this fuzzy, near-apocalyptic ten-minute rocker. [Driving Rain, 2001]

11. "Appletree Cinnabar Amber": If no one told you, there’s no way you'd guess this downtempo ambient number comes from a former Beatle. And since he barely told anyone he was half of “The Fireman" back in 1998, this hypnotic gem went completely unnoticed. [The Fireman: Rushes, 1998]

10. "Growing Up Falling Down": Sure, growing old is sad, but even at the height of his youthful powers, Paul wouldn't have had the perspective to create something like this. ["Fine Line" b-side, 2005]

9. "Cosmically Conscious": Written during the Beatles' 1968 Transcendental Meditation retreat, McCartney finally released his tongue-in-cheek tribute to the Maharishi (cf. “Sexy Sadie”) as a hidden track 25 years later. [Off the Ground, 1993]

8. “That Was Me”: Another song about the magnitude of looking back on an incredibly full life. Even here, McCartney manages to convince you that after five decades as a superstar, he’s still as wowed by it as you. [Memory Almost Full, 2007]

7. "Really Love You": With Ringo on drums, McCartney delivers a smoldering bass line and goofs around with some high-pitched echo-y singing. Listen to it above. [Flaming Pie, 1997]

6. “Sing the Changes”: On this ambient rock side project, McCartney slipped in one of his most uplifting choruses in years. “Childlike sense of wonder” indeed, Sir Paul. [The Fireman: Electric Arguments, 2008]

5. "Fine Line": Radiohead producer Nigel Godrich refused to let Paul record anything resembling treacle, forcing McCartney to craft a critically acclaimed baroque pop album—but its highlight was the joyous, jaunty “all is forgiven” opener. [Chaos and Creation in the Backyard, 2005]

4. “Ever Present Past”: The idea that his past accomplishments overshadow his present life is a heavy thought, but the crisp music here sounds as jubilant and effervescent as if he were still 23. No one does dichotomy like Paul. [Memory Almost Full, 2007]

3. "Run Devil Run" After losing his wife of 29 years, a mad-as-hell Macca went into the studio to record an album of early rock ‘n’ roll covers, as well as this unfettered original in the style of Little Richard. [Run Devil Run, 1999]

2. "How Kind of You": You don't usually think of McCartney as being “out of sorts,” so it’s nice to know he’s human after all. Aside from the fact that, unlike most of us, his moody bouts produce complex, affecting songs such as this. [Chaos and Creation in the Backyard, 2005]

1. "The Song We Were Singing": McCartney’s first post-Anthology release, Flaming Pie, found him sounding more like himself than he had in years. His palpable joy is clear on meticulously crafted songs like this one, where Paul reminisces about late night philosophizing with John Lennon. [Flaming Pie, 1997]  

What latter-day Macca songs did we miss? What's your number one? Do you strenuously object to praising any of the aforementioned tunes? Sound off in the comments below!