This is not the Frank Sinatra you know. This is not him. In the past decades, Sinatra has become rather well known as an almost mythological poster-child of wild, carefree love and infatuation as well as Christmastime music. And yes, that’s not entirely untrue. However, this is quite a different scenario we have here. For the duration of In the Wee Small Hours, Old Blue Eyes’ blue eyes brim with tears as he stays up late, late into the night, stewing in his isolation and loneliness, drowning his sorrows with self-loathing and regret. In the Wee Small Hours is a sucker punch of a record, a forty-nine-minute floodgate of despair, pioneering a formula that would become ubiquitously used by future musicians like Nick Drake, Elliott Smith, and Bon Iver. In fact, Sinatra is so unanimously remembered for his positive-thinking love songs that very few people realize that he was one of the very first musicians to release a full album of “sad music”. In the Wee Small Hours, released in 1955, also gave the whole “concept album” notion another try, even though the whole idea of concept albums wouldn’t really take off until the Beatles would experiment with it more than a decade later. It’s a dark, cold journey, so bundle up and hold your broken heart close – it’ll be your only comfort.

Like many similar records that followed, In the Wee Small Hours was created in the aftermath of an extreme personal crisis for the artist. Beginning in the early 50s, Sinatra’s popularity began a serious decline, with the loss of his original target audience and the rise of rock and roll. A suicide attempt in 1951, a failed TV show season, the loss of a record label, and the end of a marriage and several relationships only proved how bad things had gotten again and again. Picked up by a new record label, Sinatra and a minimal band convened to record the tracks on late, cold February and April nights in 1955. The process was apparently harrowing – Sinatra and the band would reportedly go on coffee the whole night, and the Singer himself would occasionally break down in tears during a session. The album, despite all odds, proved to be a resounding success, not only for Sinatra, but for the format of the “album” as art. In the Wee Small Hours is more than the sum of its parts – it transcends its status as a collection of music to become an intimate chronicle of Sinatra’s life through classic tunes.

In the Wee Small Hours has something for everyone. If you’re really into “Sad Music” and are looking for something new to stimulate catharsis, I can’t recommend this enough. The music selections, almost all selected from the Great American Songbook, are written well and executed even better. Sinatra’s natural skill in showmanship makes every song an enjoyable listen, even if it is thoroughly and profoundly “sad music”. Each song, in downtempo jazz orchestral style, positively stews with emotional negativity and cathartic pathos. Listen to the title track, with its tinkling piano, xylophone, and mournful strings. Listen to those lyrics: “You like awake and think about the girl/and never ever think of counting sheep”. The venomous self-loathing on “Glad to Be Unhappy” rivals the sharpest poison mustered by Elliott Smith or Conor Oberst many years later.

Sinatra leaves all trace of his usual love-struck mushiness behind. In the Wee Small Hours is formal and straightforward. It beats around no bush and pulls no punch. The slow, pulsing bass and strings propel the album along slowly, torturously, through Sinatra’s dark night, as he attempts to escape into dreams of his lost love (“Deep in a Dream”), then attempts to escape said dream (“I See Your Face Before Me”), and tries for love only to be friend-zoned (“Can’t We Be Friends”, and yes, this is the album where Frank Sinatra is friend-zoned).  In general, he runs madly through the endless labyrinth of heartbreak, chasing some kind of solace or distraction, pursued by a monstrous regret.

               This album’s value rises far above its ability to represent crippling heartbreak and depression, though, so don’t fret if you’re not into “sad music”. If anything, the jazz band arrangements, and Sinatra’s showmanship as a vocalist keep this record effortlessly engaging from start to finish – even if you do feel a little colder inside when it’s all over. The slow swing of “Mood Indigo” is especially lovely as a jazz tune, as well as the slow burn of “Dancing on the Ceiling” (also one of the record’s most horribly depressing songs). It’s also an album that’s important to the history of popular recorded music in general. Sinatra had always been in favor of pioneering and popularizing the format of the “album” since the beginning of his career as a recording artist, and this album can definitely be considered the high mark of an illustrious, influential career. Until then, get some sleep, Frank. There are plenty of fish in the sea.