Willie Nelson’s first career-overview boxset is called One Hell of a Ride, but that doesn’t mean the music on it comes at you fast and furiously. Taken as a whole, though, the listening experience does. There are ample ups, downs, detours and turnarounds, much like Nelson’s roughly 54-year career.

The story starts in late 1954 or early 1955, with Nelson singing “When I’ve Sang My Last Hillbilly Song”, a song that looks ahead to the future, to the end of life: “I hope and I pray you’ll forgive me / when I’ve sang my last hillbilly song.” He was 20-year-old Hugh Nelson then, not yet “Willie Nelson” the icon. In fact, the first disc could be titled “Becoming Willie Nelson”, or some such thing.

Across four packed discs, One Hell of a Ride presents the basic story of Nelson’s successful recording career, in roughly chronological order ... ”roughly” only because it’s chronological by release date, not recording date. Of course the “basic story” of Nelson’s career is anything but small and easy. The boxset’s booklet shows 92 album covers, and I’m not sure he hasn’t recorded even more. The boxset contains 95 songs off 58 of those albums, plus five non-album tracks. Setting so much music in a timeline puts the focus on Nelson’s story, on the progression of his career. Yet there’s much more than just one story here. Within the one overarching story are many smaller ones. You could listen to One Hell of a Ride from many angles, hear many stories within the transitions from one recording, and corresponding circumstances, to another. The boxset is a truncated guidebook to the maze that is Nelson’s life work.

The first disc starts with a young Nelson playing on his own, or with a few friends, first in Texas and then Portland; then with him getting a songwriting deal, writing hits for others (“Crazy” for Patsy Cline, “Funny How Time Slips Away” for Ray Price), and singing those songs himself on LPs with titles like ... And Then I Wrote. We hear him becoming a singer, getting comfortable at the microphone. Nelson is a sentimentalist at his core, behind the beard, smile and leather jacket. In this pre-beard, pre-long hair period, his forte is stately love and heartbreak ballads peppered with country flavor, and some gospel (“Laying My Burden Down”).

The end of the first disc and beginning of the second wind through the end of Nelson’s initial Nashville years, towards his “outlaw years”, the Texas years, which disc 2 gets into about half way through, after it jumps backwards into contract-obligation albums of songs recorded five or more years before their release. One of those songs, Hollis DeLaughter’s “Blackjack County Chain”, tells a prison story that fits with the “outlaw” look Nelson and pal Waylon Jennings cultivated in the ‘70s, though it’s from 1967 and is musically more representative of Nashville formula than the creative independence that is really what the “outlaw” thing was all about. Though also recorded in Nashville, 1971’s classic “Me and Paul” seems the first overt “outlaw” song, for its camaraderie, playful frankness about drug use, and life-on-the-road scenarios (“we received our education in the cities of the nation”, he sings).

Yet the other songs on Yesterday’s Wine, more mannered in form and less wild in content, are musically closer to the music that Nelson made upon breaking with Nashville. “Family Bible” prefigures the looking-back gospel of The Troublemaker, recorded in New York. And though painting a much rosier picture, the love ballad “Summer of Roses” nods towards Nelson’s love-on-the-rocks concept album Phases and Stages, as Yesterday’s Wine’s slight concept-album form pointed towards the more overt concept-album form of Phases and Stages and 1975’s Red Headed Stranger.

That latter album, the outlaw tale inevitably considered one of Nelson’s most lasting album-length statements, is barely present here. Only “Blue Eyes Crying in the Rain”, a great song with few traces of the album’s story, is included. It may not matter, as another song or two from that album wouldn’t have communicated the audacity of the project as a whole. And the mid-‘70s material on the second disc does convey what Nelson’s move from Nashville to Texas was all about: freedom.

The end of disc two showcases Nelson feeling more at ease with making music, exemplified by one of his loosest tracks ever, “Shotgun Willie”. In this period, he was feeling freer to collaborate with friends, freer to conceptualize big album-length statements, and freer to do whatever he felt like, whether it was sing jazz standards or pay tribute to heroes like Lefty Frizzell.

The third disc opens with him on tour in 1978, sounding like a superstar who has turned life into one big party. “The life I love is making music with my friends”, he famously sang in 1979’s “On the Road Again”, and that’s the spirit that drives his music in the late ‘70s and early ‘80s. He’s singing with friends (Leon Russell, Merle Haggard), covering his friends (Kris Kristofferson), writing songs for movie soundtracks, and having hit tours and hit crossover records. In 1981, his version of “Always on My Mind” hit #1 on the Country, Pop, and Adult Contemporary charts. He was still a country star, often looking back to old favorite jukebox songs and singers, but also a pop star. The extreme of the latter is witnessed through 1984’s ridiculous “To All the Girls I’ve Loved Before”, a duet with Julio Iglesias. That the song hit the Pop and Adult Contemporary charts isn’t a surprise; that its biggest success was on the Country charts, where it hit #1, is a testament to Nelson’s star power, to his larger-than-life stature by that point.

The fourth disc starts off within that life of luxury, though with Nelson’s dedication to old friends (“Highwayman”, with Johnny Cash, Jennings and Kristofferson) and his nerve (the record exec-baiting “Write Your Own Songs”) intact. The bottom falling out of Nelson’s celebrity life is exemplified by the pairing of an especially overdone “What a Wonderful World” with the spare, humble “Country Willie”, part of Nelson’s 1990 effort to pay back the IRS the mega-dollars he owed in back-taxes, Who’ll Buy My Memories: The IRS Tapes. From there, the story becomes one of Nelson returning to ensure legacy, status, and financial security. 1992’s celebrity-studded Across the Borderline was the first big “comeback” effort, though it was bested by 1998’s Teatro, unfortunately represented here by two of the less memorable tracks.

From there it’s back to doing whatever Nelson wants: covering Kermit the Frog, confidently dueting with Lee Ann Womack, doing a reggae album. Tracks from 2007’s Ryan Adams-produced Songbird, and this year’s even better Kenny Chesney/Buddy Cannon-produced Moment of Forever, one of the best albums in Nelson’s lengthy catalogue, would have fit in well here at the end, but likely didn’t make it in time. Instead, One Hell of a Ride ends looking backwards, with a track from Nelson’s fine Cindy Walker tribute album followed by a 2007 version of the song that opened the set, “When I’ve Sung My Last Hillbilly Song”. It’s a valiant effort to close the circle, to mark this as a completed story. A boxset of this scope is in part a monument, the equivalent of the massive stone statue rising from the ground for all to see and admire. But Nelson’s still moving, always on the move.

To flip through the photos in the booklet is to see Nelson everywhere: in the desert and the mountains, next to Johnny Cash, Johnny Carson, and John Belushi alike. It’s easy to start seeing Nelson as a cipher, as a Forrest Gump-like character appearing everywhere throughout time. Look closer and he appears more like a cornerstone, a fixture that the world revolves around. He changes, but at the same time doesn’t change. If the central question of One Hell of a Ride is “who is Willie Nelson?”, the answer ends up being, “He’s Willie, nothing more and nothing less.”