Note: The following was an essay written for a college course that has since been placed here for archiving.

The cultural weight of an album cover is an almost eternal detail to any EP or LP and has haunted the list of responsibilities for an artist long before our current era of imagery in media, where a good look can make or kill an artist. This is truly evident in the cover art for Frank Sinatra’s 1955 studio album, In the Wee Small Hours, his ninth and, to some, most important album.

Though often lost to the crowded list of over 50 albums released by Sinatra, many of which contained bigger hits like “Fly Me to the Moon” or “I’ve Got You Under My Skin”, the album managed to go gold on September 6th, 2002, far from the only of Sinatra’s works to do so. In the Wee Small Hours achieves its importance in a different field than many of ol’ Blue Eyes’ discography; the field of emotional and cultural importance.

The album, which reached number two, a position it maintained for 18 weeks, on the Billboard album chart, achieved much more than the usual commercial-focused success of its compatriots. The Rolling Stone Magazine article, titled the “500 Greatest Albums of All Time”, summarizes the album as a mixture of somber moods and careful planning. “The first set of songs Sinatra recorded specifically for an LP sustains a midnight mood of loneliness and lost love – it’s a prototypical concept album. Listen close and you’ll hear the soft intake of his breath.” (Rolling Stone)

The article in question awarded Sinatra’s experimental masterpiece the 101st spot in its list of 500 albums. It is the only Sinatra album in the top 250 of the list, the only other on the complete list being Sinatra’s Songs for Swingin’ Lovers, which was placed at 308. 

In the Wee Small Hours is widely considered the first great concept album, as described in Jim Cullen’s Restless in the Promised Land, “The real originator of concept albums was Frank Sinatra, who in albums like In the Wee Small Hours(1955) and Frank Sinatra Sings For Only the Lonely(1958) exploited the cultural possibilities of inherent in the then-new technology of long-playing vinyl records.” (Cullen, 98) While the concept album structure of the album is important for the music business to this day, it is perhaps the concept which the album builds around that is the most revolutionary aspect of Sinatra’s most vulnerable work. The album is commonly considered to focus on the topics of loneliness, failed relationships, and depression.

This observation is based both on the tunes and lyrics used in its contents and the events surrounding Sinatra’s life around the time the album was written and recorded. By this I refer to Sinatra’s back to back failed marriages with Nancy Barbato and Ava Gardner, who he divorced in 1950 and 1957 respectively. Gardner had been Sinatra’s mistress toward the end of the previous marriage and their relationship would itselfdeterioration due to the extramarital tendencies of both artists. Released in 1955, In the Wee Small Hours found itself buried into the midst of the toxic relationship. The publicly acknowledged connection has led the album’s many heartbroken songs to be known as “Ava Songs” (Taraborrelli, 205).

The album cover takes on the themes championed by the album’s music with a careful selection of colors, patterns, and placement. The cover portrays a detailed drawing of Sinatra himself leaning against an unidentified building while holding a lit cigarette at waist level. Sinatra is well dressed in a suit, fedora, and tie, and placed in front of a in front of a blue-tinted street, buildings and lit lamp posts on both sides, which leaves him alone in an undetailed yet clear night time scene. The Capitol Records logo is placed in a small form in the top left corner with the artist and album names written in small, thin, and white letters and in a simple font.

Sinatra appears to the viewer detailed to the point of nearing real life while his world seems lost in the middle of McCloud’s pyramid. McCloud touches on the nature of using realistic or abstract images in his book, Understanding Comics, “When pictures are more abstracted from reality, they require greater levels of perception” (McCloud, 49) Through this logic, we quickly identify and understand Sinatra’s presence, but must take more time to understand the world he finds himself in. 

The Sinatra shown to us on the album’s cover and contents, a Sinatra heartbroken and that has resorted to writing his “ava songs” to get by, is not the Sinatra most fans, contemporary or listening at the time of the album’s release, would be familiar with according to the majority of his discography. Remembered for his humble Italian roots and traditional yet crisp sense of dress, only one of the eight Sinatra albums released did not include an image of Frank Sinatra smiling. That album, Songs for Young Lovers, was released just one year before In the Wee Small Hours.

At the same time, Sinatra had become one of the famed Rat Pack, a collection of performers who shared residency in Las Vegas and performed together. The Rat Pack, on top of their reputation for popular musical performances, were both famous and infamous for their constant womanizing and heavy drinking. In many ways the group would represent everything wrong with masculinity in the 1950’s all the while gaining fans due to their Las Vegas antics, combining classic dress with constant drinking and sexual buffoonery. Left with the impression that the crooner was a smiling sex symbol surrounded by a lifestyle that represented a perfect combination of classy and fun.

The new face of Sinatra, one tortured by his extramarital lifestyle and reliance on addictive substances, would be a shocking site to any fan navigating his discography chronologically or by popularity. After all, only one song, “In the Wee Small Hours of the Morning”, from the album is featured Ultimate Sinatra, one of the most popular compendiums of ol’ Blue Eyes’ work, and none of the album’s tracks have made it on to the top ten list of Sinatra’s Spotify page, which tracks his most streamed songs. Confronted by the vulnerable side of the King of Swing and Vocal Jazz, no fan can see the same man they did when they first stumbled into the sweeping first date soundtracks and anthems of self-determination that form a majority of Sinatra’s career.

In a time when men were restricted in the field of emotional expression, In the Wee Small Hourscover provides an unexpected lighthouse as a beacon of emotional anxiety. It would not, however, work for anyone other than Sinatra himself. Sontag discusses in her book, On Photography, “the quality of feeling, including moral outrage, that people can muster in response to photographs of the oppressed, the exploited, the starving, and the massacred also depends on the degree of their familiarity with these images” (Sontag, 19).Sinatra, already a nation-wide sensation by 1955 and a symbol of contemporary masculinity and success for time, was a perfect arbiter for a message so uncommon for its time outside of the arts and so against the grain. 

Tufte writes about three key visual techniques in his book Visual Explanations, which can be used to further analyze the cover. Tufte explains the importance of quantities, as shown through these techniques, in images as thus, “Our thinking is filled with assessments of quantity, an approximate or exact sense of number, amount, size, scale.” (Tufte, 13) These techniques are direct labels, encoding, and self-representing scales. The direct labels of the album, the artist’s and album’s names along with a recording label, are what you’d expect from many albums of the time. They are all presented in a soft white color and a thin font. They seem engineered to take away as little as possible from the rest of the image and foreshadow the less-than-excited tone of the album.

The encoding of the cover comes in the form of three key colors. The first is the mild skin tone of Sinatra, a standard beige similar to his real skin color. This is used simply to make the image of Sinatra seem real and accurate. The other two colors are a light blue and a range of gray to black. The blue is a clear signifier of Sinatra’s somber mood and creates an odd parody of the singer’s otherwise charming association with the color blue, often called ol’ Blue Eyes for his crystal blue eyes. Finally, the self-representing of the album is the long and winding road which lingers behind Sinatra and disappears in the distance, the lamp posts in the foreground and background, and the buildings appearing through the haze.

These various details provide scale to the image and establish the physical world surrounding the protagonist who is otherwise existing in an emotional and mental world. Through these portions of the image we understand that Sinatra’s struggles are real and grounded, but also realize just how empty and alone he finds himself to be. 

Frank Sinatra, the gleaming diamond at the head of the Rat Pack, allowed In the Wee Small Hoursto present a version of him that didn’t drink out of joy but instead smoked away the pain. By presenting an image of vulnerability, Sinatra caught the eyes of wandering fans who expected ol’ Blue Eyes to appear jolly and colorful on every album but instead found him sunken into the night. Sinatra opens a window into the emotional vulnerability of the 1950’s man, allowing his ninth studio album to become a therapeutic experience utterly different from the swinging rhythms that made him famous.

This is a Sinatra we would not see again for many decades, only reemerging later in life as he reached his final years in the industry. To the audience of today the album, which despite its acclaim is often left out of lists of his bests or most listened tunes, provides an unexpected twist whilst discovering a classic artist. The ironic twist of the contemporary listener being that Sinatra’s experimental deep dive into his own psyche would be all to normal today, when artists regularly explore their struggles or depression publicly and in song. It was the first concept album, the first concept cover, and the first great emotional cover; it would not be the last.

Works Cited:

“Restless in the Promised Land: Catholics and the American Dream: Portraits of a                        Spiritual Quest from the Time of the Puritans to the Present.” Restless in the Promised Land: Catholics and the American Dream: Portraits of a Spiritual Quest  from the Time of the Puritans to the Present, by Jim Cullen, Sheed & Ward, 2001, p. 98.

“Gold & Platinum.” RIAA, Recording Industry Association of America, www.riaa.com/gold-platinum/?tab_active=default/award&se=In%2Bthe%2Bwee%2Bsmall%2Bhours#search_section.

Rolling Stone. “500 Greatest Albums of All Time.” Rolling Stone, Rolling Stone, 11 Oct. 2018,www.rollingstone.com/music/music-lists/500-greatest-albums-of-all-time-156826/cream-fresh-cream-172702/.

“Sinatra: behind the Legend.” Sinatra: behind the Legend, by J. Randy Taraborrelli, Grand Central Publishing, 2015, p. 205.

Sontag, Susan. On Photography. Penguin Classics, 2014.

Tufte, Edward R. Visual Explanations: Images and Quantities, Evidence and Narrative. Graphics Press, 2012.