Is this a pinnacle of pop music in the 1950s? Perhaps. We'd call this collection "standards" of the American songbook at this point, but this is a stellar album in a year that would see the ushering in of a brand new phenomenon with Elvis Presley's first album released from RCA. This combination of 40 year old Frank Sinatra and the Nelson Riddle Orchestra results in an almost flawless collection of pop classics from the legendary crooner. This is meticulous and disciplined big band swing jazz that provides a dynamic, but unobtrusive landscape on which Sinatra's peerless phrasing and timing sketches scenes of young love and passion. These songs are so ubiquitous now in soundtracks and as period pieces that it is hard to imagine what a stunning album this would have been and still is if you take the time to listen to it.

Immersing yourself in this album is the imaginative equivalent of experiencing a glamorous night out on the town without having to tip the maitre'd to get a better seat. This 1957 live recording is stunning in its execution and centers Sarah Vaughan's contralto within the fast and fluid conversation between the piano, bass, and drums. Her voice is warm and rich like a buttery caramel, and her delivery is both impeccable and playful. It's a live recording that feels intimate and authentic. It reminds you of the way jazz should be experienced - in a tailored suit or in pearls (or both, it's a free country) in a dark and smoky club. I just wish that this, rather than David Lee Roth, had been my first introduction to "Just A Gigolo."

The random album generator said, "So, you've enjoyed that swinging jazz? Let's see how adventurous you are." Attempting to assess Kanye West's cultural impact is a fraught endeavor, but we are just dealing with 2010's epic release, My Beautiful Dark Twisted Fantasy. This 2010 release is maximalist hip hop from a figure who truly believes he is larger than life. On the heels of his Taylor Swift controversy, West released a monumental album that is packed full of grandiosity and anxiety. It is equal parts self-aggrandizing and self-deprecating. West feels deeply the rush of cultural power and simultaneously fears it. For a moment, you believe he could hold the balance. But we know better at this point. Sonically, this album is stunning and bold, a creative amalgamation of sounds, guests, samples, and themes. This is not for everyone. It is at many junctures raw and vulgar. As an artistic achievement, it is a reminder within the noise of current headlines of the occasional genius of Kanye West.

"Something happened on the day he died/Spirit rose a meter and stepped aside." David Bowie's final album was released on his 69th birthday and two days before he died from cancer. Recorded in secret and without an advance press, Blackstar is watermarked with the specter of mortality. All musical recordings contain voices that are simultaneously embodied and disembodied. This is starkly real on Blackstar, where Bowie's presence and absence spiral in dance. Like his career, this album is rich with experimentation and a keen musical sensibility. Experimental jazz is marked by Bowie's ethereal voice - a voice both sonic and written - throughout this album. The soundscape is jarring, immersive, and challenging but never off-putting. All of us are in the process of writing our final chapters. Few of us are so self-conscious about our last testament. From Starman to Blackstar, Bowie continues challenging and vexing us to grasp the interplay of finite and infinite in the human condition. This album is not straightforward, but neither is life. A classic parting gift.

Remain in Light is both a feat and feature of postmodern vertigo, and David Byrne is all of us losing our shape trying to act natural. The Talking Heads, in collaboration with Brian Eno burst from the post-punk confines of New York City's CBGB club into an uncertain yet thrilling soundscape where the old maps are useless and the boundaries of genre are permeable. "The world is near, but it's out of reach." The spaces and places that used to ground us are unmoored, and we may ask ourselves, "How did I get here?" What's the soundtrack to the collapse of overarching frames of reference? It is something like this: frenetic, driving and looping polyrhythms, afrobeats and electronic droid speak, and the specter of Byrne's rootlessness. This album sees the maturation of the band's art rock into global ambitions. Our musical horizons burst open, and we found no firm place to stand, but plenty of room to dance. "My God, what have I done?"

There is a reason that so many current musicians and artists (especially those who felt marginalized by mainstream society) point to the act of watching David Bowie perform "Starman" as Ziggy Stardust on the Top of the Pops show in 1972. People saw and heard themselves validated for the first time by this bold, brash artist, seemingly unafraid of the consequences of going against the norm. And "Starman" is a messianic song, an ode to being seen and affirmed by the other. The Rise and Fall of Ziggy Stardust and the Spider from Mars is a concept album, a rock opera, and a classic testament to music's ability to lift you. Recorded after Bowie's first trip to the US, it begins and ends with show-tune anthems and, within the bookends, contains ballads, rockers, and hints of country honky tonks. It stands the test of time and never fails to lift the listener to the stars. Let all the children boogie.

If an alchemist were tasked with distilling pure sexual energy in a band frontman, they’d likely end up with Rod Stewart. Not as tawdry as Jaggar and less earnest than Daltrey or Plant, Stewart may be best described as - I don’t know - cheeky? Like he’s aware that we’re aware of the improbability of it, but he’s just gonna own it until last call. The Faces are fast, loose, and loud like your favorite bar band. This is bloozy rock where you can smell the stale beer when the needle drops. They are good while being the opposite of tight, the anti-Steely Dan. Some songs you feel like the wheels are just going to come off but the pure gravitational force emanating from the different parts holds it together without assuring us that we are out of danger. This is most emblematically felt on “Stay With Me,” the Faces breakout hit on their second album of 1971, which is anything but a love song. It winds up, takes off, slows down, careens, and pulses with intense energy that never takes itself too seriously. Stewart shares lead vocals with Ronnie Lane, who contributes Debris, a touching ode to Lane’s father. It’s a standout track, but honestly, it is Stewart’s brashness meshed with the Faces’ loose electricity that makes A Nod Is As Good As A Wink…To A Blind Horse a must listen.

Around the time she struck a pose, I stopped listening to Madonna. It was nothing personal. We'd just drifted apart, I thought. We were both getting older, and the shock value was starting to wear off. Sure, I'd revisit the Material Girl if I needed a hit of that nostalgia from high school days. But mostly, I left her work in the rearview mirror. This made listening to Ray of Light for the first time such a revelation. This 1998 album is the club album U2 had hoped they would make with Pop (an album for which I still harbor great affection), a reflective journey through the deeper questions of life that wouldn't seem out of place amid pulsing lights and technobeats on a sweaty dance floor in downtown Miami. Madonna succeeds where U2 fell short because she doesn't come down from the clouds to address the messiness. Instead, she begins in the sinewy sensuousness and lets it lead her to contemplative heights. One of Madonna's gifts is the discipline to stay within her voice's confines and never push beyond her own boundaries. This places the electronica and mesmerizing beats into the forefront as she raises the questions of life, joy, fulfillment, and depth without us having to leave the dance floor. The coyness of the early 80s transforms into a spiritual seeking at the end of the decade that fronts authenticity over artifice.

I was unaware of this album prior to the 1001 Albums generator's recommendation. Jazmine Sullivan's Heaux Tales is a bold and intimate declaration of women's agency, needs, and desires in the often-murky world of relationships in a patriarchal society. This is arresting R&B fronting a powerful female presence, a power alternately expressed in agency and vulnerability. The songs are interspersed by spoken soliloquies from different women adding to the power of the project overall. This deals with some frank stuff, but is an illuminating glimpse into how the frameworks of gender roles and relationships can be explored and troubled.

Album art is a tricky thing. It can give you insight into the psyche of the artist, possibly giving you a clue to the tenor and tone of the album. Stephen Stills's self-titled debut album cover gives you a sense of the quintessential seventies singer-songwriter - a pensive, sensitive soul pouring out a vulnerable masculinity over acoustic strings. Maybe this package is wrapped in the dulcet hushes of the Laurel Canyon sound, perfected so well by Stills and his compatriots in Crosby, Stills, & Nash. But the cover belies the festival of sounds exploding from the grooves on the black lacquer of the disc inside. The album reveals the musical depth of Stills' range and talent, a talent often overshadowed by Neil Young's grungy cantankerousness or David Crosby's infamous alienating personality. Contained within are gospel-flecked hymns to common humanity, classic seventies love songs, muddy blues guitars, and a host of all-star collaborators, including Nash, Crosby, Jimi Hendrix, Booker T. Jones, Eric Clapton, Cass Elliot, and Rita Coolidge. While the opener (Love the One You're With) may resonate with a sense of dissatisfaction, the closing song (We Are Not Helpless) contains the soaring challenges I need to hear this week. " Open up, my friend, and learn to hear." It's a call to feast on this album. A call to not give up on this collective grand experiment. Those who have ears, let them hear.