It’s late, and you’re tired, and there are miles and miles to go. You’re driving a car you love, despite its crappy gas mileage and the fact that your contemporaries are all driving hybrids. You cruise through highways and back roads, through marshes with your windows down, despite the sharp odor of salt water and decay. You drive downtown, but you’re just cognoscente of the motorcyclist in front of you not to hit him. Miles to go, and you’ve fallen into one of those hellishly contemplative moods, where thoughts race around your brain like a dog chasing its tail. Thoughts like: I wonder how I managed to either completely miss or downright toss away any chance at real love. But Jesus Christ, what would I have done if I had found it? The mood’s like a drug, endlessly depressing and endlessly fascinating. So this list is for you and your habit. Tonight, these songs are for you:

Top 5 songs for the late night, melancholy drive:

1. “Goodnight, California,” Kathleen Edwards
The real trick to this alt-rocker comes half way through at 3:06, when the actual singing stops, and the hypnosis begins.

2. “Overnight Drive (What Might Have Been),” *64
Made up of elements from Angry Salad, *64 continued the tradition of writing infectious pop/rock tunes. But “Overnight Drive” seems to perfectly encapsulate a feeling of loneliness that every touring musician must sometimes feel with simple but beautiful lyrics like, “A cigarette explodes on the highway in the dark.”

3. “One Headlight,” The Wallflowers; 4. “Can’t Run But,” Paul Simon
Both songs evoke a state of melancholly with a sense of urgency brought on by the songs’ tempos. For “One Healdlight,” it’s the droning guitar punctuated by bass and snare. In “Can’t Run But” you have Simon’s mello voice augmented by a near-frantic thumb piano.

5. “Wish You Were Here,” Pink Floyd
The fade-out at the end of this track makes you believe you could, at some point, simply run out of road and fade out among the stars.

Runners up: “Precious Things,” Tori Amos; “Dead Flowers (Live in Calgary),” Steve Earle (Rolling Stones cover);”Your Ex-Lover Is Dead,” Stars; “We Are Pilots,” Shiny Toy Guns; “Comfortably Numb,” Pink Floyd

Overnight Drive (What Might Have Been) (Sample download)

Top 5 songs for the late night, melancholy drive