Whiskey River Usually the opening song at Willie's live performances, "Whiskey River" is another one of those tracks so closely associated with Nelson that many forget he didn't write it. Penned by Johnny Bush, Willie recorded the song in 1973 for his album Shotgun Willie. Interestingly, the song didn't become a bona fide hit until five years later when Nelson included in on Willie and Family Live. Whatever its origins, "Whiskey River" remains a Nelson classic, a lively tale of loss and remembrance. --Darryl Smyers

Bloody Mary Morning From Phases and Stages, the greatest concept album about divorce ever, this is a sad, but romping drinking tune that is every bit as fun - whether it should be or not -- as "Whiskey River." --Kelly Dearmore

Beer For My Horses Though this song was co-authored by Toby Keith, it's still a rousing ditty, perfect for summoning the courage needed to play a high school football game or some other war based activity. -- Brian Rash

Gravedigger Although not written by Nelson, his cover of dude-bro diplomat Dave Matthews' '03 track is a one-up on the original. Nelson is the perfect narrator for this tale of forgotten souls. --Lee Escobedo

City of New Orleans This Steve Goodman-written classic has been covered by many of the greats but, it's impossible to accept this tune coming from anyone else's voice at this point. Willie and train songs go as well together as Willie and certain herbal remedies. (KD)

The Maker As adventurous as Willie has always been, few albums represent his lack of concern for sonic boundaries as his excellent, Daniel Lanois-produced 1998 record, Teatro. Oddly enough it's this Lanois-penned tune that stands out the most on the record. Lanois' production and Nelsons nasal tone blend to hypnotic effect in this oft-overlooked tune. (KD)

Blue Eyes Crying In The Rain This song, written by Fred Rose and made famous by Willie, is one of the most beautiful, strolling moments of his classic 1975 album, The Red Headed Stranger. (BR)

If You've Got the Money, I've Got the Time Willie has always paid wonderful tribute to his heroes. In this Lefty Frazell tune, Willie plays no games and just shoots his lover straight with "And if you run short of money, I'll run short of time." (KD)

The Highwaymen A tale of a soul living four different lives, in four different eras all meeting an untimely end is the song the brought together Country's ultimate super group. A highwayman, a sailor, a dam builder and an astronaut, four verses, sung by four of country music's most enduring legends: Willie Nelson, Kris Kristofferson, Waylon Jennings and Johnny Cash. It's pretty much perfect. --Jaime-Paul Falcon

On The Road Again When it comes to venturing out on the open road in search of whatever you may or may not be looking for, subjectively, there is no better song to start that playlist. (BR) Angel Flying too Close to the Ground Recorded for the film Honeysuckle Rose, "Angel" is such a great song that even Bob Dylan covered it. The song would be Nelson's seventh number one on the country charts, and it is one of the best country singles of the '80s. Nelson has claimed the song is about both his wife Connie and a friend who died in a motorcycle wreck. Either way, it's a transcendent moment in Nelson's storied career. (DS)

My Heroes Have Always Been Cowboys Another country classic penned by Sharon Vaughn but made famous by Willie, this song was on the soundtrack to The Electric Horseman, as is his other classic, Mama, Don't Let Your Babies Grow Up To Be Cowboys. (BR)

Reasons to Quit A beautifully sad Willie/Merle duet that's long been overshadowed by "Pancho and Lefty," from the same 1983 album, Matthew Houck's Phosphorescent reminded people of all ages how timeless this tune is on his 2009 gem, To Willie. (KD)

To All The Girls I've Loved Before As a kid, I remember this song playing in my parents car right after church, and that may be the reason I wasn't all that fond of it back then. But it is a moving, tender song, and Willie and Julio Iglesias make an oddly charming pair. (BR)

Mr. Record Man Legend has it that Willie Nelson tried to sell the rights to "Mr. Record Man" for $10 to a Houston club owner, instead the owner gave him a $50 loan and a job playing the club six nights a week. Very much a song from the late 50s era of pop influenced country, "Mr. Record Man" tales the tale of a forlorn lover trying to track down a blue song he heard and connected with. We've all been there, and that's what makes Willie the best--he's been there, too. (JPF)

Night Life A bluesy and honest account of one man's beautifully painted, albeit bleak portraiture of the downtrodden barfly, "Night Life" was country music star Ray Price's hit and title track from his 1963 album of the same name. But the experiences and rich narrative was all Willie's. Bordering on more blues than country, this classic has been covered by many artists over the years. --Aaron Ortega

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Crazy It's ironic that perhaps Nelson's best song is actually more famous for Patsy Cline's (spectacular) performance of it. The song is a showcase of Nelson's wonderful songwriting ability and penchant for capturing the madness of being in love. (LE)

The Scientist Leave it to Willie Nelson to take an overly saccharine song from one of the worst bands to ever get popular and make it amazing. Willie's distinct voice adds an extra level of solemness to the song's tale of woe, and the backing vocals and pedal steel turn it from merely sad to crushing. (JPF)

Help Me Make it Through the Night One of several Kris Kristofferson tunes that Willie expertly interpreted, this sexy song showcased Willie's continued lack of concern of industry-establishment conventionality. (KD)

It's Not Supposed to be That Way Also from the male-perspective of the divorce story, which makes up Phases and Stages, Willie painfully surrenders instead of mustering the will to fight any longer for the marriage that's crumbled. (KD)