Ten Great Albums for Two in the Morning

When you find yourself awake in the middle of the night, alone with your worries, music can help you make it through. But not just any music. Only a 2:00 a.m. record album will do.

A 2:00 a.m. album keeps you company in the darkness while you wrestle with fear and watch the dull glow of the stereo lights. A 2:00 a.m. album does not necessarily uplift you: a brass band marching through your living room feels wrong in the wee hours, which is why Sgt. Pepper’s Lonely Hearts Club Band cannot be a 2:00 a.m. album. But 2:00 a.m. music does not drag you over the emotional abyss, either; Joy Division’s relentlessly depressing Closer needs to stay on the shelf after midnight. What you need is a friend who keeps you company without overstepping their boundaries. Albums like these:

1. Only the Lonely

Frank Sinatra once said, “I like recording late at night. The later the better. My voice was not made for daytime use.” Ol’ Blue Eyes recorded Only the Lonely in 1958. Today it feels like a time capsule that he left for future generations to discover during the lonely hours. Hearing the interplay between his crooning voice and Nelson Riddle’s orchestral arrangement is like sipping a warm cup of tea. The songs, such as the gentle “What’s New” and “Willow Weep For Me,” comfort your soul. Sinatra called these songs “saloon songs” because they feel perfect when you’re alone in a bar with a blinking beer sign. They work just as well in your home. When he sings “Excuse me, while I disappear” on the song “Angel Eyes,” you want to go where he’s going. And stay there.

2. The Dark Side of the Moon

David Gilmour makes Dark Side a 2:00 a.m. album. There’s the keening wail of his pedal steel guitar. And his low voice, soothing and reassuring, even as he sings Roger Waters’s lyrics that dwell on the pressures of everyday life. I realize that Dark Side might fall into the too-bleak-for-late-night category for many; it works for me because the album absorbs and reflects fear and melancholia like that friend I mentioned who simply keeps you company in the night. And that’s all because of Gilmour. If you want to feel loathing and anger, try Pink Floyd’s Animals. For paranoia, give The Wall a spin. But for 2:00 a.m. anxiety, I’ll see you on The Dark Side of the Moon.

3. Automatic for the People

The quiet reflection of “Night Swimming.” The emotional transcendence of “Everybody Hurts.” The bittersweet longing in Michael Stipe’s voice. The haunting respite that a quivering electric piano and guitar provide in “New Orleans Instrumental № 1.” I pick up something different each time I listen to this brooding masterpiece. And each time, when Michael Stipe sings, “If you feel like you’re alone/No, no, no, you are not alone,” I feel like he’s right there in the room singing to me.

4. Spirit

Listening to Willie Nelson is like eating a heaping plate of comfort food. The album, true to its name, takes you on a spiritual journey. Many of the songs consist of nothing more than Willie and a guitar sounding like he’s hanging out on a country porch with his family gathered around. When he sings “Too Sick to Pray,” he sounds like a Psalm writer having a conversation with God. The moment when he asks, “Remember the family Lord, I know they will remember you,” is as intimate and endearing as anything you’ll ever hear on a record.

5. Strange Days

The Doors have recorded a lot of perfect 2:00 a.m. songs. There’s “Riders on the Storm,” exuding dark dread. The ethereal “Crystal Ship.” But Strange Days is the one Doors work that endures as a 2:00 a.m. album from start to finish. The moment you hear Ray Manzarek’s creepy Moog synth playing on the opening track, you are transported out of your world and into the universal mind of the Doors. Jim Morrison’s voice, like David Gilmour’s on Dark Side, makes the album. He’s powerful without overpowering you on “When the Music’s Over,” and soft as a whisper on “You’re Lost Little Girl.” It’s a dark album. But its surreal undercurrent keeps Strange Days from passing into the realm of the overly foreboding.

6. Hounds of Love

Kate Bush’s idiosyncratic vocal delivery meshes with the lush arrangements to make you feel like you’re floating weightless somewhere in the clouds. In the dead of night, I can dig a sensation like that. On the opening song, ‘Running up That Hill,” a delicate bed of synthesizers and drums pulls you into Kateland before her voice soars and dances across the music. This album rewards the listener with unexpected, breathtaking moments, like the glorious choral section from the Georgian folk song “Zinzkaro” that makes “Hello Earth” a balm. Maybe it’s the way that her voice soars on every song, but Hounds of Love makes me feel hopeful.

7. Substrata

This ambient exploration of mood from Biosphere is unlike anything on this list. Substrata uses samples of running water, creaking wood, blowing wind, human voices, reverb, echo, guitar, and synthesizers to create a strange sonic landscape that is, quiet, provocative, and even menacing. I listened to this album often after I became a father and spent many late nights watching over my newborn.

8. The Trinity Session

The Cowboy Junkies recorded The Trinity Session in one night using a single microphone in Toronto’s Holy Trinity church. The church itself is like another instrument whose acoustics enhance Margo Timmins’ gentle voice. Her a capella reading of “Mining for Gold” creates a kind of loneliness that feels right — not desperate, but melancholy enough to make you feel like she understands your 2:00 a.m. solitude.

9. Kid A

Those descending chords from an electric piano that open Radiohead’s Kid A offer a clue about what comes next: synth, heavy bass, and voice distortion. I’ve never been able to enjoy Kid A in broad daylight. Thom Yorke’s dissonant but affecting vocals, processed by Pro Tools, sounds like your head does when off-kilter thoughts collide in the night.

10. All Things Must Pass

George Harrison understood what being awake at 2:00 a.m. means. On “Beware of Darkness,” the 10th song on All Things Must Pass, he sings, “Watch out now, take care/beware of the thoughts that linger/Winding up inside your head/The hopelessness around you/In the dead of night.” Like Willie Nelson’s SpiritAll Things Must Pass is a meditation on matters of faith. It’s heavy, dark, and reflective. But it’s also hopeful. On the title song, George sings, “Now the darkness only stays the night-time/In the morning it will fade away/Daylight is good at arriving at the right time/It’s not always going to be this grey.” Those words lift the soul at 2:00 a.m., and they can carry you into the day that lies ahead if you let them.

Parts of many other albums work well, too, such as Led Zeppelin III (for the bucolic vibe of Side Two) and Sticky Fingers (“I Got the Blues” is mandatory for a 2:00 a.m. playlist); In addition, Wish You Were Here belongs on a 2:00 a.m. album list, but I wanted to represent artists besides Pink Floyd on my Top 10. What do you listen to at 2:00 a.m., and why?

Why I Listen to Bad Sinatra

On a cold November afternoon, I’ve immersed myself in a bad Frank Sinatra album from 1974, Some Nice Things I’ve Missed. Why would I do that? Because experiencing an artist’s lesser work helps you understand them better, like reading chapters of a revealing biography.

Some Nice Things I’ve Missed gives me a deeper sense of how Sinatra tried to remain relevant during his comeback following a brief retirement in the early 1970s. Sinatra, pushing 60, was recording less and performing more, especially in Las Vegas, where Elvis Presley had entered the final phase of his own career. On Some Nice Things I’ve Missed, Sinatra tried to capitalize on the popularity of several songs that were charting during his retirement. He covered everything from Tony Orlando and Dawn’s “Tie a Yellow Ribbon ‘Round the Ole Oak Tree” to Jim Croce’s “Bad, Bad Leroy Brown,” both of which were hits in 1973.

Here, Sinatra was attempting to force a sense of contemporary relevance by chasing popular tastes. And he failed miserably. The 10 songs he chose were unsuited for the orchestral treatment given to them by the album’s producer and arranger, Don Costa. And he interpreted the music with indifference, at best. For example, his phrasing on “Bad, Bad Leroy Brown” sounded forced and rushed, lacking the warmth and humor of Jim Croce’s original.

The problem was that he allowed desperation to cloud his judgment. Instead of choosing songs that played to his strengths as a vocalist, he used a song’s proven chart position as the litmus test for covering it. As a result, to modern-day reviewers, Sinatra “sounds disinterested in the project, as if he can’t wait to leave the studio,” in the words of reviewer Stephen Thomas Erlewine.

Now let’s go back to 1967, when Sinatra, in his early 50s, was staring down the threat of rock and roll. Although he committed mistakes that he would repeat on Some Nice Things I’ve Missed, he also recorded a masterpiece, Francis Albert Sinatra & Antonio Carlos Jobim, that was unlike anything he’d ever done.

Jobim was a leading composer of the bossa nova style of music that had gained a global following of its own. On Francis Albert Sinatra & Antonio Carlos Jobim, Sinatra discovered a new direction with sensitive, nuanced performances on songs such as, “The Girl from Ipanema” (for which Jobim shared a composing credit). Sinatra sounded cool and relevant, because not only was the genre hip, but he also sounded hip. As biographer James Kaplan wrote in Sinatra: The Chairman, “Sinatra sang with an exquisite tenderness he hadn’t tapped since The Wee Small Hours, 12 years before.”

In fact, Frank Sinatra created a timeless sound that has outlived a lot of rock and roll from that era. I’ll take Sinatra singing “The Girl from Ipanema” and “Quiet Nights of Quiet Stars” over Iron Butterfly’s “In-A-Gadda-Da-Vida” any day. He didn’t try to compete with rock and roll. Instead, he explored territory that no rock and roller could touch.

Listening to Frank Sinatra at the top of his game is one of life’s great pleasures. But listening to bad Sinatra invites more inquiry into his life, too. Bad Sinatra makes me appreciate the insecurities and struggles of a man who fears being irrelevant as he grows older. If you’ve never felt that insecurity or fear that Sinatra experienced — trust me, my friends, that day will come. On your best days, you will respond with grace. But sometimes you will stumble, as Sinatra did. Listening to Sinatra struggle on an album such as Some Nice Things I’ve Missed makes him more human and relatable.

I love Sinatra when he’s brilliant. I get Sinatra when he fails.

How James Kaplan Paints Music with Words


Every once in a while, a book comes along that makes you want to become a better writer. You cannot always predict when those breakthroughs will happen. A case in point: James Kaplan’s two-volume biography of Frank Sinatra, Frank: The Voice and Sinatra: The Chairman (the latter of which was published in October 2015). I read the sprawling books to immerse myself in one of the most storied lives in show business. And although Frank Sinatra’s life makes for riveting reading, with its dramatic peaks and valleys, Kaplan’s lyrical phrasing, like Sinatra’s singing, shimmers, soars, and inspires.

Sinatra’s story is well known, and Kaplan covers it all: his rise of greatness as a teen heart throb, his breathtaking fall from the top, his return from nowhere with his Oscar-winning performance in From Here to Eternity, the torch he carried for Ava Gardner, his seedy association with the Mafia and pathetic relationship with John Kennedy, and, of course, the performance and recording of some of the greatest works of singing in the 20th Century or any century for that matter.

Kaplan shares one juicy anecdote after another, such as Sinatra’s cringe-worthy temper tantrums and dustups, cocktail swigging, high rolling hijinks with fellow rat packers, and transcendent moments in concert and the studio. Other biographers have covered this ground, too. But Kaplan goes beyond telling stories to share his own insight on Sinatra, thus adding the context of meaning, as in the following:

He lived with loneliness: the solitude of the only child who grows up with inexpressible feelings of otherness, the self-inflicted isolation of the man who’d brutally pushed Lauren Bacall away, the aloneness of the great artist who mused on the sonorities of Ravel and Ralph Vaughan Williams while feeling compelled to pal around with hoodlums . . . He was a kind of hunger artist, one who starved himself so the rest of us could feel better about our own hunger.

In one passage, Kaplan expresses both Sinatra’s contradictions and appeal through the lens of loneliness, one of the defining attributes that would shape his life, and essential to understanding his art and his actions. Elsewhere, Kaplan calls upon some kind of extraordinary writing muse to drop brilliant phrases on the reader like polished word diamonds. For instance, Kaplan describes the complex web of relationships in Sinatra’s life as his “strange orbit.” Ava Gardner, for whom Sinatra infamously left his wife, Nancy (triggering his career nosedive in 1950), “kept a kind of pilot light of agitation burning in his life.”

Of Judith Campbell Exner, the call girl who Sinatra introduced to John F. Kennedy, Kaplan writes, “The light of truth bends around her presence in any historical narrative, because of the gravity of her known associations — with Frank Sinatra, Sam Giancana, and John F. Kennedy.”

When Kaplan takes the measure of Sinatra’s music, he also descriptively and vividly, as when he describes Sinatra’s voice, worn down after a demanding tour in the early 1960s, as “a gorgeous ruin, deep and resonate, but hoarse and cracking periodically.” Kaplan’s triumph is capturing the essence of the songs Sinatra recorded — their color and impact — without getting tangled in technical jargon. Instead of describing sound, he paints impressions. For instance, he describes the 1961 Sinatra collaboration with arranger and conductor Billy May on Swing along with Me thusly:

From the rip-roaring castanet camp of “Granada” (May actually had his sidemen chant “cha-cha-cha!” at the end) to Frank’s magic-carpet-like vocal soaring over the twinkling, tinkling Arabian-bazaar melodrama of “Moonlight on the Ganges” to the thrill of the closer, “You’re Nobody ’til Somebody Loves You,” which starts as a caress and finishes as a powerhouse, a sprit of sheer fun infuses the Reprise LP, showing to what heights this artist was capable of ascending when he was artistically engaged.

He captures the legendary interplay between Sinatra and his musical collaborators with a keen ear for how words sound to the reader, as well as an eye for imagery, as in this description of the song “Lady Is a Tramp”:

Sinatra gave the tune a loving, lilting reading at a medium-swing tempo, launched by Bill Miller’s deliciously inventive piano reading (improvised and not written, and showing the great keyboardist, as in many other instances, to be his boss’s musical equal). Then, opening like a great jewel box, comes Riddle’s terrific chart, with its sequential reveals of strings, woodwinds, and brass (including Harry “Sweets” Edison’s dulcet, minimal trumpet fills).

Another writer might have provided a more technical description, as author Jonathan Gould often does in his book about the Beatles, Can’t Buy Me Love. For instance, in discussing the Beatles song “Happiness Is a Warm Gun,” Gould writes, “In the second section, where the harmony equivocates between A major and A minor and the meter equivocates between 9/8 and 12/8 time, John [Lennon] seems to inhabit this predatory character.” There is nothing wrong with Gould’s style; he’s simply assuming a certain amount of musical knowledge on the reader’s part. Although it’s clear that Kaplan is steeped in the arcane language of music, he chooses a more impressionistic style with phrases such as “opening like a great jewel box.”

When he writes about music, James Kaplan crosses the line from impressing me to inspiring me. I often write about music, but I typically write about the music industry as opposed to music itself. Describing music can be intimidating. The writer must find a way to convey for the reader’s eyes an abstraction meant for the ears. Kaplan has challenged me to push myself to get better at this most demanding act of writing. A recent blog post I wrote about The Revenant music score is the result, and I am going to find more opportunities to write about music. Thank you, James Kaplan.

What books have inspired you to be a better writer?


Why marketers love bad boys

Why do bad boys and girls fascinate us? Why do people who thumb their noses at society and sometimes self-destruct capture the attention of marketing and business executives?

I’ve been pondering these questions ever since I saw Dana Anderson of Kraft Foods discuss “The Bad Boys’ Guide to Digital Bliss” April 5 at the Forrester Research Marketing Forum.

Dana riveted the audience by discussing how bad boys like Robert Downey, Jr., and Jack Nicholson can teach marketing executives valuable lessons about living with swagger and embracing the art of being sly. It was fascinating to see an executive from a staid brand like Kraft hold up bad boys as examples for business leaders to follow — and equally fascinating to witness an audience of staid marketing executives eating out of the palm of her hand.

Dana was an excellent presenter, to be sure. But I believe the topic of itself was irresistible to those of us who live in the weeds and wrestle with such weighty topics like how to build our brands with social media. In truth, we love bad boys because they are sexy, they break rules, and they are, well, cool.

Bad boys are sexy

Bonnie and Clyde. King David and Bathsheba. These couples behaved very badly. And their stories are undeniably sexy. According to the Bible (a great journal of bad boy behavior) Bathsheba, the wife of Uriah the Hittite, attracted the attention of King David by bathing in public view of his palace (akin to Monica Lewinsky flashing her thong at President Clinton).

David, a man whose life was defined by bloodshed and passion, promptly seduced her, got her pregnant — and then conspired to have Uriah killed so that he could have Bathsheba all to himself.

Poor Uriah: loyal to his wife, loyal to King David, and apparently far too boring for his Bathsheba and not compelling enough to make David think twice about bumping him off. Uriah is nothing more than a footnote to history. But David and Bathsheba? We remember David as one of the great kings of Israel, and Bathsheba the mother of wise Solomon. They were dangerous, destructive, and sexy.

Bad boys make their own rules

Even the most daring and creative marketers and business leaders live by rules. We have processes for developing ideas. We create our own structures for getting work done every day.

Bad boys fascinate us because they create their own rules for succeeding. They thumb their noses at us, and we reward them with our fascination and interest.

It’s hard to believe now, but in the 1950s, Elvis Presley was viewed as a bad boy. And there would be no modern day rock and roll had Elvis Presley not broken all the rules for how a white entertainer (circa 1954) was supposed to sing and behave. He dressed differently, he sang differently, and he behaved differently.

White male singers were not supposed to dress in gold lame suits and shake their hips on stage. They were supposed to sound like Bing Crosby and Frank Sinatra: safe, romantic, and white. But Elvis broke all those rules (the most important being that he was a white person who sounded black).

Alas, Elvis stopped being a bad boy when his manager Colonel Tom Parker steered his career in the direction of safe, boring movies like Clambake and Harum Scarum. And then for a brief moment in the late 1960s, Elvis recaptured the public’s interest. How? By appearing in a dangerous, skin-tight black leather suit in a memorable Christmas special in 1968 and taunting his fans with a sneer and a swagger. He was a bad boy again – for a while.

Bad boys are cool

Is it the way they embody rebellion? Or is it their ability to laugh at their own bad boy behavior while wallowing in it? I don’t know exactly. But bad boys are cool.

Defining cool is like defining pornography: you just know it when you see it. Jack Nicholson in the 1960s and 1970s was cool. He winked at his fans as he sneered at authority. Robert Downey, Jr., is cool for a different reason: he takes his own bad boy behavior in stride.

On the other hand, Axl Rose and Mel Gibson are uncool because they spew rage (especially Gibson) and try too hard to be “dangerous” (Rose). True bad boys capture our interest because they seem so effortless, natural, and even self- effacing. There is something in us that wants to be cool.

Do bad boys fascinate you? Why? Check out some highlights of Dana’s presentation here and let me know how you feel about bad boys.