What does summer sound like? John Prine, Frank Sinatra, Martha and the Vandellas

Here we are at the crossroads of summer, the unofficial half-way point of a season long championed for its sense of outdoor invitation, vacation-inspired escape and, in all senses of the word, warmth.

It’s also a time marked by some of the most expressive pop music ever designed. Ever since rock ‘n’ roll was accepted by mainstream audiences, songs – mostly, youth-oriented ones – have been concocted to bankroll the vivid but, for many, short-lived sense of celebration that surround those months when school has been dismissed and the sun beckons us.

With that in mind, we’re offering a summer playlist as a soundtrack for the season. This one, though, doesn’t simply revisit popular summertime pop hits or obvious stylistic examples of surf and beach music. Well, maybe we included a few standards, but the idea here was to span the ages and well as sentiments.

The playlist covers music made every decade since the 1930s, running from pop to jazz to folk to Brit-pop to mambo. Some reflect all the joy you would hope for from the season, while others are a few shades darker – reality checks, if you will, examining a slightly more unsettling shade of summertime.

These 20 songs aren’t presented chronologically, but rather, as a true playlist should, in an order that hopefully represents a well-rounded journey. Sometimes, the mood is party-like. Sometimes, it’s rebellious. Sometimes, it’s simply sad.

Now, let’s get this summer trip started.

War – “Summer” (1976)

The final hit of the veteran soul band’s ’70s hit parade for the United Artists label. A street party slice of Latin-tinged soul that modestly yet profoundly encapsulates the groove of the season.

The Kinks: “Sunny Afternoon” (1966)

Ray Davies turns a saga of an old-money scoundrel left in the proverbial poorhouse by British taxation into a decidedly non-rock hit with a vintage ballroom flavor. One of the Kinks’ finest works.

Billie Holiday – “Summertime” (1936)

Gershwin’s classic aria from “Porgy and Bess” has been recorded countless times, but it was Lady Day who first took it to the pop charts. Over 85 years later, its seasonal glow has not faded.

Dire Straits – “Twisting by the Pool” (1983)

In an about face from Dire Straits’ elegantly grim 1982 album, “Love Over Gold,” band chieftain Mark Knopfler quickly cut a follow-up EP disc featuring this ultra-giddy, vintage-flavored beach anthem.

The Lovin’ Spoonful – “Summer in the City” (1966)

Okay, so this is one of the obvious entries, but it’s simply too perfect of a summer song to neglect. A pop blend of urban disenchantment and psychedelic jubilation.

Chuck Prophet – “Summertime Thing” (2002)

Indie pop-rock scholar Prophet has been making great records for nearly three decades. This one, a perfectly crafted, leisurely paced confection, is among his most popular works.

The Motels: “Suddenly Last Summer” (1983)

One of the most expertly designed pop tunes of the ’80s. It’s also one of the most unassuming – a sleek, slick seasonal reflection written and sung by Motels empress Martha Davis.

Jason Isbell and the 400 Unit: “Dreamsicle” (2020)

As with so much of Isbell’s music, “Dreamsicle” abounds with exact imagery. The song presents a photographic depiction of a smalltown summertime along with the underlying necessity of leaving it.

Sly and the Family Stone – “Hot Fun in the Summertime” (1969)

Another concession to the obvious camp. But, honestly, how anyone not be taken by such a breezy, joyous soul celebration of summer? It sounds as brilliant today as it did at the close of the ’60s.

The Ramones – “Rockaway Beach” (1977)

The Ramones may have made up one of the cornerstone bands of the punk rock era, but they were also beach bums at heart as this two-minute, two-chord party outburst dictates.

The Mavericks – “Summertime (When I’m With You)” (2015)

Mix a little mambo with a swirling splash of old school pop and toss in a guitar/organ groove to ignite, everything and you have a slice of ultra-cool summer fun from the genre-jumping Mavericks.

Bill Monroe and his Bluegrass Boys: “Summertime is Past and Gone” (1948)

As delicate as it is despondent, this harmony-rich reverie travels a lonesome road. One of the first recordings bluegrass patriarch Monroe cut with Lester Flatt and Earl Scruggs.

Martha and the Vandellas: “Dancing in the Street” (1965)

From the dark trails Monroe traveled, we hit sun-soaked streets criss-crossing America with this exuberant chart-topper from the golden age of Motown. An obvious but unavoidable entry.

Tom Waits – “The Last Rose of Summer” (1993)

This is about as sweet and subtle a song as you’ll ever hear drop from Tom Waits’ lips. A woozy, melancholy lullaby penned for the theatre project (and, later, album) “The Black Rider.”

Frank Sinatra: “Summer Wind” (1966)

The idea of sliding from Tom Waits to Frank Sinatra just seems right, you know? Especially when you’re talking about one of the most impeccably orchestrated and vocally expressive hits of his career.

Alice Cooper – “School’s Out” (1972)

There’s a bit of the juvenile delinquent in all of us, an inner upstart who can’t help but cheer on Mssr. Alice’s classic anthem of academic emancipation. “We’ve got no class and we’ve got no principles.”

Fairport Convention: “Summer Before the War” (1988)

An obscurity, but one worth checking out – a light, lovely remembrance of lost youth by this veteran British folk-rock band. The title reveals a state of bliss with a fast approaching expiration date.

Eddie Cochran – “Summertime Blues” (1958)

The temptation was strong to instead go with The Who’s 1970 haywire reworking of this tune, but why slight the animated teen angst Eddie Cochran cooked up on the original version?

Beach Boys – “Surf’s Up” (1971)

“Surf’s Up” is the antithesis of the typical Beach Boys song. The inventive harmonies and composition are there, but the sentiments reflect a season that trades fun in the sun for reflection and melancholy.

John Prine – “Summer’s End” (2018)

Somehow, this one couldn’t be avoided. Though beautiful, the song is also a statement of loss. That we lost Prine to COVID-19 in 2020 makes it even sadder. A powerfully moving season closer.