Bruce Springsteen's been married to Patti Scialfa for 19 years — they celebrated their anniversary in Winnipeg this week (the couple is there to cheer on their 18-year-old daughter Jessica Springsteen in a national horse show-jumping competition). So at first and second glance, it seems like The Boss has been pretty lucky in love.

But maybe not always — for songs 90-81 in the Ultimate Springsteen Countdown show that Bruce certainly understands heartache and regret. These are some of the most searing tracks of Springsteen's career. They also pay at least small homage to musical characters as diverse as The Beach Boys and Phil Spector.

Song 90: “Livin' in the Future”

Album: Magic

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The E Street Band reunited for "The Rising" in 2002, but I would argue that the classic E Street Band sound didn’t return until five years later with this track off Magic. The groove is lifted straight from “Tenth Avenue Freeze Out,” with Clarence’s burly sax still blowing Bruce down the street just as it did 30 years earlier.
 
The lyrics are a study in denial. Even with all of the walls of his life crumbling down upon him, the narrator tricks himself into believing everything is fine in the chorus with his own little imaginary time machine: “We’re livin’ in the future and none of this has happened yet.”
 
Even the band is in on the ruse, negating the dire lyrics with a good-time assault that even features some happy-go-lucky “sha-na-nas” at the end. Only Danny Federici’s organ solo lets some anguish in, wailing into some darker corners the rest of the music refuses to go.
 
“Livin’ in the Future” is Bruce’s good-natured poke at those who try to gloss over their personal problems and the problems of the world with a shrug of their shoulders, suggesting that such an attitude in this day and age isn’t just foolish, it’s downright dangerous. A direct hit on those people might have seemed too harsh and too much of a downer, so Springsteen effectively sideswipes them with the help of the E Street Band’s righteous noise.
 
 
 Song 89: “Jackson Cage”
Album: The River

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 Bruce Springsteen has always had a knack for dissecting the lives of the downhearted. “Jackson Cage” is one such character study, an incisive look at a girl whose life is a prison that’s caused only in part by circumstance. His point here is that sometimes people can be beat down so much that they fail to realize that there’s a way up, and they end up only contributing to their own misery.
 
“Jackson Cage” is one of the many songs on The River that are all about the economy and efficiency of the package; it’s why the album is one of the rare double albums that doesn’t feel bloated. The band sinks their teeth into a tight arrangement with all the pieces interlocking brilliantly. Bruce also zigs when you would expect him to zag in the instrumental section by dropping a harmonica solo into the thunderous rock background.
 
The lyrics are effective because they don’t pull any punches. Bruce’s words make it clear of the consequences here: “Every day ends in wasted motion/Just crossed swords on the killing floor.” This doesn’t seem like hyperbole, because this girl is dying inside little by little.
 
Springsteen wails in the lead-up to the chorus with the strangled voice he used on "Darkness On The Edge Of Town", valiantly trying to get through to this girl. He knows that ultimately it’s up to her to turn the key, but his powerful argument at least should show her to the door.
 
 Song 88: “Hearts of Stone”
Album: Tracks

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They all came out of the woodwork in the early 80’s. There was John Cafferty & The Beaver Brown Band. Billy Vera & The Beaters. Davy Crockett & The Wild Frontier. OK, I made that last one up, but if you guessed that the first two were bands that rode Springsteenmania to moderate success in that time period, you win the prize. (And you watched way too much MTV as a kid, but, then again, I’m a proud member of that club too.)
 
Anyway, they could never make the harder-rocking sounds work in my estimation, because they lacked both the inestimable chops of the E Street Band and Bruce’s songwriting genius. But they could kinda sneak by on the slow ones by imitating Bruce’s lower, soulful register and throwing in a little sax, hence hits like “Tender Years” or “At This Moment.”
 
The ironic thing is that Bruce’s own version of this type of slow one, which blows all the imitators out of the water, never made it to the charts because it never even made it onto an album. “Hearts Of Stone,” recorded during the Darkness On The Edge Of Town sessions, certainly didn’t fit there, but I think The River, in all of its diverse sprawl, certainly could have accommodated it. Instead, the song stayed on the shelf until it popped up on Tracks and floored the faithful.
 
Bruce has his reasons, of course, so it’s best to just enjoy this melancholy classic now that we have it. Featuring Bruce and Little Steven’s distinctively disheveled harmonies and The Big Man’s emotional solo standing out amidst the brass, “Hearts Of Stone” finds Bruce lending comfort to a former love even though he’s moved on (“I can’t talk now, I’m not alone.”) The can’t-go-home-again moral is as old as time, but it’s rarely been delivered with such charisma and grace. Hear it once, and you’ll never settle again for anything less than the original.
 
 Song 87: “Valentine's Day”
Album: Tunnel of Love

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To end an album filled with doubt and misgivings about romance in all its guises, Bruce Springsteen wrote one of the most desperately romantic songs of his career. The title of the song is almost ironic, though, because Springsteen spends most of the song singing about the love he’s missing. His holiday isn’t filled with candy and flowers, it’s filled with nightmares and moonlight rides on desolate highways.
 
The ambling tune and gentle acoustic guitars are a bit neutral. They’re quiet enough to soothe but the melody never quite resolves into a comforting refrain, suggesting an endless journey. The music really pales here next to the fascinating lyrics, which are dense with imagery and ripe with longing and lack.
 
It’s a complicated narrative. You can read it as a man who has found true love and can’t abide anything else in his life that pulls him away. But he sounds so fearful of losing her that his grip on their romance seems tentative at best.

The descriptions are harrowing for what’s ostensibly a love song: his heart “pounding, baby, like it’s gonna bust right on through;” the “spooky old highway;” “the cry of the river” or “the cold river bottom.” The narrator seems to have more in common with the fallen leaves stranded on the cold ground than he does anything else. Maybe that’s why he feels jealous of a friend who recently became a father; at the very least, it’s a source of unconditional love.
 
In the final verse, Bruce awakes from a vivid dream and wonders what startled him from his slumber: “It wasn’t the cold river bottom that I felt rushing over me/It wasn’t the bitterness of a dream that didn’t come true/It wasn’t the wind in the grey fields I felt rushing over me/No no baby it was you.”
 
So the question remains: Is he saying that this woman provides a contrast to all of these disturbing dreams or is she reminiscent of them, hence the confusion? That uncertainty cuts to the core of what Tunnel Of Love is all about, and it’s why, even on “Valentine’s Day,” Bruce just couldn’t be sure about love.
 
 Song 86: “A Good Man is Hard to Find (Pittsburgh)”
Album: Tracks

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Bruce writes from the perspective of a war widow in this heart-tugger that stayed unreleased until Tracks. Many of the details could have applied to just about any song about a woman who misses her man. Springsteen subtly slips in the opening lines about the weather in Pittsburgh, contrasting the weather in Saigon to establish the particulars, and then he lets the emotions tell the rest of the tale.
 
The arrangement is a bit of an odd duck. Garry Tallent’s bass line has the kick of a classic Motown ballad, but Roy Bittan’s piano is strictly Bakersfield country. Somehow it all comes together, though, propelled by Springsteen’s empathetic vocal.
 
Only once does he let some anti-war sentiment overtly slip into the lyrics, even as it’s implied the whole way. In the final verse, the woman, after tucking in the daughter who’ll grow up without her dad, can’t hold back her frustration anymore: “Well she thinks how it was all so wasted/And how expendable their dreams all were.”

The show of emotion is all the more powerful because of the strong façade she had put up throughout the song. And, in that moment, the song becomes much deeper than just a simple lament for a lost loved one. It’s a sad testament to the fact that soldiers aren’t the only ones who have to make the ultimate sacrifice in times of war.
 
 Song 85: “The Ties that Bind”
Album: The River

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This actually could have been the title song to a proposed 1979 release by Bruce, but he shelved it and incorporated the material into The River. As it is, “The Ties That Bind” makes an energetic and airtight opener to the album, a winning homage to some of Springsteen’s '60s favorites.
 
The intricate, clean guitar work of Bruce and Little Steven is reminiscent of The Byrds or the guitar-weaving of Brian Jones and Keith Richards on some of the Stones’ 60s hits. There are also times when the song is a soundalike for the classic Searchers’ smash, “Needles And Pins.” The bridge, with its stuttering drums, hearkens back to Phil Spector’s classic productions, an antecedent Bruce had already honored quite handily on “Born To Run.”
 
The main thing that you get from “The Ties That Bind” is that crisp, sharp sound and hooks galore. The lyrics get their point across concisely, because any extraneous verbiage would have damaged the radio-friendly effect. Bruce stresses on this song to a girl that it’s difficult to go it alone, and that she one day might miss the bonds that she has formed, even unwittingly, in her life.

That theme is a common one on The River, but nowhere was it expressed with more urgency and vitality than on this thrilling throwback.
 
 Song 84: “Working on the Highway”
Album: Born In The U.S.A.

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I saw Bruce on the Other Band tour in Syracuse, NY in the early '90s. At the end of a typically monstrous three-hour extravaganza, Springsteen looked ready to wrap up when a fan in the first few rows handed him a New York license plate with “BRUCE” on it.

Seeming genuinely touched, he yelled out something like “We can’t stop now” and led the band into a turbo-charged version of “Working On The Highway,” sending the crowd into exultation.
 
It’s interesting that this song has become such a good-timey type of track, because a close inspection of the lyrics betrays its origins as one of the songs from the Nebraska sessions. The sad-sack protagonist is like a cousin of Johnny 99. And the same dark tendencies that prevail upon the Nebraska characters are there as well: “Some heading home to their families, some looking to get hurt/Some going down to Stovall wearing trouble on their shirts.”
 
The story is ingenious in that this guy’s destiny remains unchanged no matter how he tries to alter it. He’s fated to work on a road gang be it in a 9 to 5 slog or in prison, which is where he ends up after getting involved with a jailbait girlfriend.
 
“Working On The Highway” was given the gloss that brightened up the Born In The U.S.A. tracks for mass consumption. The band takes what could have been a brooding folk song and turns it into an exhilarating rave-up courtesy of the guitar licks and hand-claps which recall Eddy Cochran’s “Summertime Blues.”

That’s a pretty good comparison, because the two songs share a common sensibility: Societal frustration expressed in cathartically jubilant terms.
 
 Song 83: “Straight Time”
Album: The Ghost of Tom Joad

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Giving voice to a character that wouldn’t normally be considered sympathetic isn’t an easy thing to do. Bruce does it wonderfully on this brooding number off The Ghost of Tom Joad. While many would just write this ex-con off as another recidivist criminal, Springsteen gets inside his head and dares the listener to understand him, even if they don’t approve.
 
Even after paying his debt to society, this guy never shakes the stain of his prison stay: “Seems you can’t get any more than half-free.”

How can a guy try to stay clean when he’s got an uncle tempting him with easy money and a wife who doesn’t quite trust him with their children after so many years on the right path?
 
The final verses seem to suggest that the dark side is winning out, as he casually alters a hunting gun to make it more efficient for less traditional uses. The chorus makes it clear which way he’s leaning: “Got a cold mind to go tripping ‘cross that thin line/I’m sick of doing straight time.”
 
The unemotional, stoic reading of the vocals only adds to the song’s chilling effect, as does the atmospheric music. E Streeter Danny Federici lends a hand with the subtly stirring keyboard work, and distant violin and steel guitar accents are like apparitions in the background haunting this guy. “Straight Time” makes you feel for this character’s plight even as you cringe in anticipation of where his life is headed, which is no small songwriting feat.
 
 Song 82: “This Life”
Album: Working On A Dream

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Bruce takes a cosmic look at romance on this straightforward love song off "Working On A Dream." Even the creation of the universe pales in comparison to the sight of his girl: “The beauty in the neighborhood/This lonely planet never looked so good.”
 
The '60s references throughout this 2009 album are plentiful, and here The Beach Boys get their due respect from Bruce and the gang. The open, which is almost a nonsequitur from the remainder of the song, is pure "Pet Sounds" dream-pop. Later on, the backing vocalists chip in a few “ba-ba-bas” in classic Wilson brother fashion.
 
The chorus is a stirring one and the high point of this song. Bruce’s melodic skills never get much credit, but when he concentrates on the tune, as he does here, the results can be breathtaking. Even Brian Wilson would have to be impressed.
 
 Song 81: “New York City Serenade”
Album: The Wild, The Innocent, & The E Street Shuffle

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On an album full of epics, Bruce went all-out for the closing track of The Wild, The Innocent, & The E Street Shuffle and pushed the length to almost 10 minutes, still the longest track of his career. It’s a credit to Springsteen’s skills as an arranger that “New York City Serenade” never feels overlong. It’s a proper tribute to the city, capturing all of its romance and heartbreak.
 
It does so mostly through its music, because the story is just a series of vignettes, snapshots of characters taken as you’re passing by. There’s a young couple in love with each other and with their foolhardy and dangerous schemes to hit it big. There’s a hooker with the heart of stone and the guy who tries to take her away from it all.

And there’s the jazzman commenting on it all like some omniscient narrator. Bruce sketches them in miniature and lets us guess how their stories will turn out.
 
The music tells the tale well enough anyway. We’ve talked at length how Springsteen understood even at this early point in his career about how to craft his songs, especially the long ones.

Here the instruments are introduced one by one, starting with David Sancious’ unforgettable piano, one of the most memorable instrumental turns on any Bruce song. It alternates seamlessly between classical and jazzy in the dramatic intro before fading into the sad tinkling melody of the main part of the song.
 
After that, you’ve got Bruce’s strummed acoustic guitar, then some bongos, then the cinematic strings. Indeed the whole thing has the feel of a motion picture score, ambling along nicely before rising to sudden explosions of feeling.

At these points in the song, like when the Fish Lady refuses to join the narrator on the train, the music rises to meet the import of the small but crucial decisions made every day in the city, decisions that eventually define these characters. In turn, these characters, and this monster of a song, define the city.

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