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Sam SmithEXPAND
Sam Smith
Courtesy of EMI

Sam Smith's Seven Saddest Sad Bastard Songs

There is a famous line from Kurt Vonnegut’s time-traveling World War II satire, Slaughterhouse-Five, which reads, “Everything was beautiful, and nothing hurt.” It's an ironic sentiment the author believes to be the perfect epitaph for his gravestone.

For both Vonnegut and humanity, this is of course untrue, and no one knows that better than English singer/songwriter Sam Smith. In fact, based solely upon his music, his epitaph might read, “Everything was beautiful, and everything hurt.”

Pop is brimming with what we will call Sad Bastard Music. Smith, a rare vocal talent and genuinely delightful celebrity, seems to bathe nightly in the gloom and melancholy of this sub-genre. Aside from his incredible voice, one of the reasons his music is so appealing is that his stories and his heartache are relatable to anyone who isn’t a soulless robot.

But what are Sam Smith’s most Sad Bastard songs? And considering that he trades in different flavors of sadness, when is it appropriate to listen to each song? Read on for seven different answers to those questions — one for each day, so you can stay in your feelings all week long.

1. “Stay With Me.” Much of Smith’s debut LP, In the Lonely Hour, centers on unrequited love and destructive behavior. In the case of "Stay With Me," that behavior is a one night stand and the quick emotional attachment the speaker develops immediately thereafter. “Stay With Me” is the song that solidified Smith’s status as a genuine pop star as the single topped the charts and garnered plenty of accolades, including a Grammy. It also proved his ability to tell a universal story about the nature and spirit of humans as social creatures. The sort of “clinginess” he describes in “Stay With Me” is familiar to anyone who's ever felt the pangs of romantic loneliness. The desire to hold and embrace a warm body (or be held and be embraced) in a big, cold bed originates from the primal instincts of comfort, protection, and safety. The problem is, nothing could be more fleeting than a one night stand. Those minutes and hours of intimacy are so impermanent, practiced by people who are desperate to flee before the proverbial clock strikes midnight and shit gets real.

Listen to it when: You’re horny, but you also want a hug and someone to cook you breakfast in bed.

2. “Drowning Shadows.” On the extended re-release of In the Lonely Hour, we get “Drowning Shadows,” which is almost a sequel to “Stay With Me.” In it, Smith proposes the not wholly original idea that dating sucks. Casual hookups, going on dates with a variety of people, partying all night and getting drunk with friends while making new, sometimes sexy, friends, is great for a while. But for many, it gets old quick. At a certain point in most people’s lives, they reach the crossroads “Drowning Shadows” does, asking the same questions Smith posits: “Go home to nothing or stay out for more? / Give in to someone or lock down my door?” It’s a tough choice for someone who wants a more substantial experience, but also doesn’t want to go home to an empty place. Perhaps this is why Smith told Zane Lowe of Beats 1 Radio, that “it’s the saddest song I have ever written.” “Drowning Shadows” is also a melodic cousin to Des’ree’s 1997 orchestral ballad, “Kissing You,” off of the soundtrack to William Shakespeare's Romeo + Juliet. It borrows all the same rising and falling drama, allowing shifts in the narrative to be directed by both Smith’s vocals and the piano keys.

Listen to it when: You’ve taken the Uber home, the room is spinning a little, and you know you made the right choice to ditch the party and heat up some leftovers in a place where no one is around to judge, whether you eat over the sink or in bed so you can binge watch Grey’s Anatomy. Again.

3. “Midnight Train.” Sometimes there is no smoking gun when a relationship ends. No one cheated or strayed. There was no betrayal and there were no outright lies. Instead, perhaps more painfully, there are moments where it is just right to end things, regardless of how much it hurts. A career gets in the way; long distance is too much to handle; one or both partners have fallen out of romantic love. On “Midnight Train,” our narrator, who according to several interviews is not Smith himself, makes the difficult choice to call it quits with someone he still loves very much. He gives neither us nor his lover an explanation, saying only, “Love you so much that I have to let you go / I’ll miss your touch and the secrets we both know / But it would be wrong for me to stay / And I’ll just give you hope.” It’s akin to the frustrating breakup line, “it’s not you, it’s me.” Worse yet, he's already met the parents (“Am I a monster? What will your family think of me? They brought me in, they helped me out with everything”) which always complicates things.

Listen to it when: That funny, fluttering butterfly feeling you once welcomed in your belly is now a permanent, uncomfortable knot in your stomach.

4. “Say It First.” Although Smith claims this is the first happy love song he’s ever written, there is a fundamental undercurrent of sadness throughout it. He opens with the verse, "I never feel like this / I’m used to emptiness in my heart / And in my arms.” This is someone who, rather pathetically, only knows loneliness. The title of the song is a command signifying that since he does not how to handle this newfound experience of someone reciprocating his feelings; he is going to need that person to say “I love you" first. It is an attempt to protect his heart. As anyone who has ever put up emotional walls, or anyone who has attempted to storm those fortifications, knows, this can be a tough start to a relationship. The longer those walls are up, the greater the chances their would-be lovers will tire and leave, exhausted and out of love.

Listen to it when: You need a reminder that taking a chance might blow up in your face, but it could also lead to something great (because even stubborn assholes need love).

5. “Nothing Left For You.” Not all sad songs have to be slow burners. Several of Smith’s songs on The Thrill Of It All share the contrasting quality of sounding uplifting but are lyrical downers. “Nothing Left For You” finds Smith neck deep in comfortable territory: a majestic, soulful, gospel-backed confessional. This is an admission to himself, and warning to his new beau, that not only did his heart break when he gave it to “a goddamned fool,” but that he was completely and irrevocably broken as a person in the process as well. The heaven bound chorus only helps to emphasize his rising falsetto, both giving it all and illustrating just how drained he became after a past relationship he is incapable of moving on from.

Listen to it when: You’ve sabotaged a promising relationship before it even had a chance. Idiot.

6. “Not in That Way.” Rejection is the cornerstone of unrequited love. It's the slow, quiet death of a crush when the object of affection hasn't so much as thrown a wink towards the afflicted. Aschenbachs the world over watch their Tadzios from a distance, before shriveling up like day-old cocktail shrimp, crippled by their own inaction. Then there's the brave soul who presents his heart in hand, only to have it cruelly slapped away. “Not in That Way” finds our narrator putting himself out there, professing his love to someone who responds with “I love you but.…” It is perhaps the most deflating conjunction in the English language. Somewhere between a lullaby and a slow dance song from the 50’s, “Not in That Way” is also remarkable for its sparse composition. There are only two instruments here: the gentle guitar and the tormented voice of Smith.

Listen to it when: It’s raining outside and inside. And by inside we mean your face, where you’re experiencing a crying jag so violent your ab muscles hurt.

7. “Good Thing.” In an interview with Digital Spy in 2014, Smith said, “’Good Thing', for me, is the darkest song on the record. If you actually listen to my vocal, I'm not even trying to sing or sound pretty because I was so upset and sad. I kind of loved that and I feel like it really came across in the song.” Once again he revisits the notion of rejection, except in this case it is very real and very current for the singer. This song is the equivalent of seeing your old selfies with an ex suddenly pop up on Facebook, dredging up feelings that feel freshly sharpened to cut once more. Moreover, with its soaring strings, “Good Thing” has some dramatic, Frank Sinatra flourishes embellishing the pain.

Listen to it when: You know that bottle of wine will not survive the night, and you’re very okay with that.

Sam Smith. 8 p.m. Saturday, July 14, at American Airlines Arena, 601 Biscayne Blvd, Miami; 786-777-1000; aaarena.com; Tickets cost $31 to $121 via ticketmaster.com.

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