"SWEET JANE" THE VELVET UNDERGROUND (1970)

In a lot of ways, The Velvet Underground was the protypical rock & roll band. They seemed to represent everything core to rock & roll. But on the other hand, they also rewrote the rules. They didn’t play it straight. And they gave way to bands like Sonic Youth, Wilco and others to do the same—to be melodic and experimental at the same time. “Sweet Jane” is maybe one of the best examples of this, turning a three-chord rock song on its head with the opening 15-second cacophony.

“Anyone who's ever had a heart wouldn't turn around and break it. And anyone who's ever played a part wouldn't turn around and hate it.”

"EXHUMING MCCARTHY" R.E.M. (1987)

You’d be hard-pressed to find a bad song on Document. There are songs here that are legendary. Everyone will remember “It’s the End of the World as We Know it” and “The One I Love”. But “Exhuming McCarthy” is absolutely unforgettable with its driving beats, bass hooks, and unique musical personality. It was distinctly R.E.M. in sound, but it also had its own identity. It sounded like it was a blast to perform and record - and it’s still a blast to listen to over 30 years later.

“You're sharpening stones, walking on coals to improve your business acumen.”

"KAMERA" WILCO (2001)

A musical monument of the 2000s, Yankee Hotel Foxtrot first made its appearance one week after 9/11. It’s the album that put Wilco on the map. I had the pleasure of hearing a few of the songs performed live. But “Kamera” was always one of my favorites. It didn’t have the experimental side. No musical cacophony explosions on this track. But it displayed Wilco’s chill, folk side as good as any other song they’ve written.

“I need a camera to my eye, to my eye reminding which lies have I been hiding.”

"A HAZY SHADE OF WINTER" SIMON & GARFUNKEL (1968)

A little less folksy. A little less tempered. A little more gutsy. A little more attitude. When I first heard Bookends, “A Hazy Shade of Winter” was the song that reinvigorated my mood and warmed me up faster to the broader Simon & Garfunkel catalog. There’s a reason why The Bangles chose to cover it, as opposed to “Punky’s Dilemma” or “Old Friends”. “A Hazy Shade of Winter” showed a rock & roll side to the duo as they rode on a wave of popularity with The Graduate soundtrack.

“Hang on to your hopes, my friend. That's an easy thing to say. But if your hopes should pass away, simply pretend that you can build them again.”

"VIDEO GAMES" LANA DEL REY (2012)

“Video Games” is one of the more unusual pop songs of the era. But it’s also one of the most defining tracks of our time as well. While everything else went electronic, Lana Del Rey went with string arrangements. They went ecstatic, she went melancholic. Her vocals brought us back to another era. Her lyrics brought us into a vulnerable, awkward picture of a one-sided relationship. It’s these tensions within “Video Games” that make me listen to it over and over again.

“Open up a beer and you say, ‘Get over here and play a video game’.”

"FOOLS GOLD" THE STONE ROSES (1989)

It takes a certain level of confidence - maybe even cockiness - to put out an 8+ minute song. Zeppelin, Floyd, Maiden, Metallica and The Who have all done it. And the Stone Roses were no exception. “Fools Gold” was the nearly 10-minute long, psychedelic, jammy finale from one of the best debut albums of the era. Mani, John Squire and Ian Brown held their own, but it was Reni on drums who stole the spotlight from beginning to end.

“I know the truth and I know what you're thinking.”

"BORN OF FRUSTRATION" JAMES (1992)

In the early 90s, my musical experience was shaped by Nirvana, Pearl Jam, Jane’s Addiction, Smashing Pumpkins, among others. All great bands in their own right. But James flew under the radar for me. That whole time, they were steady, consistent and absolutely clear on their identity. And “Born of Frustration” was one of their best, elevating beyond the grunge agenda with James’ vigorous falsetto vocals and memorable trumpet accompaniment.

“All this frustration. I can't meet all my desires. Strange conversation. Self control has just expired.”

"(GHOST) RIDERS IN THE SKY" JOHNNY CASH (1979)

This is maybe not the first song you’re reminded of when you think of Johnny Cash. There were all the country classics and then the monumental covers, most notably Cash’s haunting interpretation of Nine Inch Nails’ “Hurt”. But in between those two signature phases was this song that epitomized the thing I’ve always loved most about Cash. That deep and unforgettable bass vocal. There’s nothing else like it in music history.

“A bolt of fear went through him as they thundered through the sky. For he saw the riders coming hard and he heard their mournful cry.”

"PULASKI AT NIGHT" ANDREW BIRD (2013)

I’ve seen Bird perform this a handful of times at various venues—from Terminal 5 to Brooklyn Steel. What strikes me most about the song is its versatility. It was the beautiful violin arrangements that won me over at first. While I’ve seen both full string performances and stripped-down versions, later I came to realize it’s Bird’s love letter lyrics to his hometown of Chicago and the melody that it dances along to that I love most about “Pulaski at Night”.

“I paint you a picture of Pulaski at night. Come back to Chicago. City of, city of light.”

"WISH YOU WERE HERE" PINK FLOYD (1975)

It wasn’t your typical Pink Floyd, neither falling within the prog rock era or their hard rock catalog. Nonetheless, “Wish You Were Here” was one of their best, most memorable songs - even deemed by Waters and Gilmour as being one of their finest collaborations. It’s one of my favorite Floyd songs of all time because it struck an emotional chord and went surprisingly minimal, allowing just the melody, lyrics and unforgettable guitar riff to shine.

“We're just two lost souls swimming in a fish bowl year after year.”

"MLK" U2 (1984)

There are no entrancing guitar riffs from The Edge here. No percussion barrage from Larry Mullen Jr. Just a reflective ode to the one and only Martin Luther King, Jr. from Bono. It flies in the face of everything that we see happening in the world - not just musically, but thematically. The Unforgettable Fire had quite a few unforgettable songs, but “MLK”, as the final track on the album, quietly and thoughtfully grabbed our attention and conscience in the most understated way.

“Sleep tonight and may your dreams be realized.”

"INSTANT CRUSH" DAFT PUNK (2013)

On Random Access Memories, Daft Punk collaborated with everyone from Pharrell to Panda Bear. My favorite is “Instant Crush” with Strokes frontman Julian Casablancas. Mind you, it didn’t have the same distinct Daft Punk electronic feel or the same distortion-soaked Strokes sound, but it balanced the two worlds rather well. Casablancas wrote the lyrics, sang them and played guitar—and behind it all were the steady, prodding Daft Punk electric jolts and hooks.

“The summer memory that just never dies. We worked too long and hard to give it no time.”

"ONE HEADLIGHT" THE WALLFLOWERS (1996)

Yesterday, my Mental Jukebox played Dylan. Today, I’m playing Dylan’s son. This was, by far, the most impactful and memorable Wallflowers song. In 1996, it was king. I remember toward the end of one night at a party, when almost everyone had left and all the booze was done, me, my friend’s sister and her friend - an unlikely trio - kept going with this song into the wee hours of the night, dancing and grooving without saying a word to each other.

“Come on, try a little. Nothing is forever. There's got to be something better than in the middle.”

"BLOWIN' IN THE WIND" BOB DYLAN (1963)

The most powerful thing about this classic song is this: “Blowin’ in the Wind” is written and sung with the wisdom and reflection of a much older man. But Dylan was only 21 when he wrote and recorded it. It’s the lead track from one of the most celebrated folk albums of all time. “Blowin’ in the Wind” wasn’t just played in concert halls either. It has gone on to take on greater meaning—sung everywhere from church gatherings to civil rights movements.

“How many times must a man look up before he can see the sky? And how many ears must one man have before he can hear people cry? Yes, and how many deaths will it take 'til he knows that too many people have died? The answer, my friend, is blowin' in the wind.”

"REMEMBER ME" DIANA ROSS (1971)

Right on the heels of The Supremes era came a solo album that carried strands of connective tissue back to her iconic Motown roots. The brass arrangements and harmonies felt reminiscent of The Supremes, but there was also an evolution in her sound. In “Remember Me'“, Diana Ross took an Ashford & Simpson composition and brought us a rendition that’s as bright, lovely and nostalgic as the lyrics themselves.

“Remember me when you drink the wine of sweet success and I gave you my best. Remember me every song you sing. Remember me as a good thing.”

"THUNDERBOLT'S GOODNIGHT" JOSH RITTER (2017)

Music has the ability to change our mood and mindset. At least the good, powerful stuff can. “Thunderbolt’s Goodnight” is that kind of song. The pandemic hasn’t been exactly a restful time. But this song reminds me to reflect on what’s most important and slow down enough to catch the beautiful moments in life. Its contemplative nature makes it a tune best played at night. “Thunderbolt’s Goodnight” is the calm after the storm.

“Take this feeling, take my dark and reeling mind from these poor words. Find a meaning far deeper than these clumsy lines.”

"THERE IS A LIGHT THAT NEVER GOES OUT" THE SMITHS (1986)

One weekend during high school, I bought The Queen is Dead” cassette and then played it non-stop that very same night. An album this good only comes out maybe once a decade. And “There is a Light That Never Goes Out” was the lynchpin to the whole thing. Many great Smiths songs seem to be composed of stories of odd, sad characters and stunning guitar riffs by Johny Marr. But “There is a Light…” created something moodier, more orchestrated, more epic. This is my favorite Smiths song of all time.

“Take me out tonight because I want to see people and I want to see life. Driving in your car, oh, please don't drop me home because it's not my home, it's their home and I'm welcome no more.”

"SAY IT AIN'T SO" WEEZER (1994)

A couple of summers ago at Jones Beach, I caught both the Pixies and Weezer in one epic night. It was like stepping into a time machine, diving into the catalog of two of the most respected bands of their era. “Say It Ain’t So” remains, in my mind, the quintessential Weezer anthem. While “Hash Pipe” rocked hard and “Island in the Sun” laid low, “Say It Ain’t So” shifted from languid to lightning with some of the band’s best guitar playing and storytelling.

“Say it ain't so. Your drug is a heart breaker. Say it ain't so. My love is a life taker.”

"THE FUNERAL" BAND OF HORSES (2006)

One of the most powerful things about music is emotional dimensionality. And in music history, you can point to dozens of songs that teeter back and forth between the quiet and reflective and the sonic and voracious. But in my opinion, few do it as well as Band of Horses’ “The Funeral”. Death is a complicated thing, representing emotions as far apart from each other as the two musical states played out on the record.

“At every occasion, I'll be ready for the funeral.”

"LEAVING ON A JET PLANE" PETER, PAUL & MARY (1967)

Some of the best songs ever written are based on simple human experiences. John Denver powerfully captured the simple act of going away on a trip and all the emotions that it triggers, and then Peter, Paul and Mary elevated it. Listening to “Leaving on a Jet Plane” is like stepping inside a time machine. It’s a microcosm of the 1960s, capturing everything from the free spirit and sentimentality to the musical style and production approach reminiscent of the decade.

“I hate to wake you up to say goodbye, but the dawn is breakin'. It's early morn. The taxi's waitin'. He's blowin' his horn. Already I'm so lonesome I could die.”