Closing Time is a special album because it features a vulnerable Tom Waits who stands much shorter than the towering musical beast he would become.
The album is an honest illustration of a man staying up late and pondering his life. The cover shows Waits leaning against his piano in the shadows, one hand gripping his hair and the other a fist pressed down on the instrument, where cigarettes and alcohol also have their resting places. There is a subdued anxiety to this picture that prepares one for Waits’ contemplations. 
The song that has stayed with me since I first heard Closing Time is the opening track, “Ol’ 55.” Even though its story is as simple as Waits leaving the house of his lover at 6 a.m., it is as much about watching the world come alive as it is about love. Perhaps the most endearing quality of the song is, ironically, the pain of leaving behind a moment that should last forever.
Most of the album follows the lead of “Ol’ 55:” modest but solid instrumentation and pensive songwriting. “I Hope That I Don’t Fall In Love With You” is heartbreaking in its theme of missed opportunity, anchored by gentle acoustic guitar. Drunken trumpets accompany Waits in the frustrated “Virginia Avenue:” “Lemme tell you that I’m dreaming to the twilight / This town has got me down / Seen all of the highlights / I’ve been walking all around.” Waits lets his mind wander 40 years into the future on “Martha,” an imagining of how two old lovers are going to reminisce. Another song that stands out from the pack is “Ice Cream Man,” an energetic sexual metaphor. The title track is different as well in that it’s an instrumental, but its melody captures the loneliness and hope of Waits’ music more effectively than any other song.
By all means, this album is not a casual listen. Waits’ lyrics can take one to dark and regretful moments, but Closing Time isn’t one-sided. Throughout the album, you get the sense that Waits knows he’s in a rough spot but that life is worth living – precisely the reason why this one gets better with age.