Eminent Hipsters

1. Early Musical Guides: Boswells and Mancini

Ellie had very specific taste in popular singers.

Discovering early jazz. The author's mother, a former swing singer, introduced him to the innovative vocal harmonies and rhythmic phrasing of the Boswell Sisters, whose work he later saw as rivaling Duke Ellington's. His cousin Barbara exposed him to hard bop jazz in her basement.

Mancini's cool influence. Henry Mancini's omnipresent film and TV music, particularly the cool jazz sound of Peter Gunn, served as an accessible entry point to modern jazz for a suburban kid. Mancini's scores, with their spare instrumentation and sophisticated arrangements, created a "Disneyland of Cool" that spoke to the author's sense of otherness amidst the conformity of the 1950s suburbs.

Beyond the mainstream. Both the Boswells, with their subversive genius applied to popular songs, and Mancini, popularizing West Coast jazz sounds, represented artists operating outside or creatively exploiting the mainstream, shaping the author's early aesthetic sensibilities.

2. Sci-Fi, Paranoia, and the Search for Null-A

The Father-Thing, though, affected me on a much more personal level.

Cold War anxieties. Growing up in the 1950s and 60s, the author was deeply affected by the pervasive paranoia of the era, fueled by events like the Cuban Missile Crisis and depicted in sci-fi stories like Philip K. Dick's "The Father-Thing" and Invasion of the Body Snatchers, which mirrored fears of communist infiltration and losing one's identity.

Seeking psychological defense. A. E. van Vogt's sci-fi novel The World of Null-A, based on Count Alfred Korzybski's General Semantics, offered the concept of a "cortico-thalamic pause" – a way to process information serenely, free from cultural programming and emotional preemption. This idea resonated as a potential defense against the perceived mendacity and conformity of the adult world.

The map is not the territory. Korzybski's core idea, "The map is not the territory," highlighted the danger of confusing words or descriptions with reality, a concept the author found increasingly relevant in a culture saturated with hype and "truthiness," leading to a sense that language no longer described real life.

3. Jean Shepherd: Radio Voice of Alienation

He was definitely a grown-up but he was talking to me—I mean straight to me, with my twelve-year-old sensibility...

A trusted adult voice. Jean Shepherd's late-night radio monologues on WOR became a crucial lifeline for the author and other alienated young people, offering a blend of Midwestern storytelling, urban cynicism, and social observation that felt authentic and trustworthy amidst the media's "hooey."

Lessons in observation. Shepherd's routines, covering childhood tales, army experiences, radio adventures, and contemporary commentary, taught the author about:

• Social observation and human types
• The omnipresence of hierarchy
• Joy in struggle and bliss in art
• The codes inherent in "trivia"
• The transience of desire

The artist's mask. Shepherd's on-air persona, while warm and charismatic, hinted at a deeper, more complex individual. The author's later experience seeing Shepherd perform live revealed a desperate need to impress and a strain of grandiosity, leading to the realization that the artist's persona is often a protective mask, and "Things are not what they seem—including me."

4. Navigating the Mythic World of Jazz Clubs

Once upon a time, the jazz club was a mythic place that signified urban romance, free-loving hipsterism and the Dionysian rites of the Exotic Black Man: in short, the dread possibility of ecstasy.

The reality vs. the myth. Visiting jazz clubs in New York City as a teenager, the author found the reality to be only partly aligned with the myth. While the Village Vanguard hosted giants like Miles Davis, Sonny Rollins, and Charles Mingus, the audience was a mix of serious fans and uncomfortable tourists, highlighting the tension between artistic intensity and mainstream discomfort.

Encounters with legends. The author witnessed powerful performances and had memorable interactions with musicians like Charles Mingus, who lectured the audience, and Jaki Byard, who graciously answered questions. He also saw patriarchs of early jazz like Earl "Fatha" Hines and Willie "The Lion" Smith, whose music carried the weight of history.

Changing times. The jazz club scene evolved with the times. The rise of folk and rock music drew audiences away, and the increasing militancy of the civil rights movement influenced the music. By the 1980s, the scene returned, but in "wholesome club environments" lacking the raw, sometimes chaotic energy of the earlier era, with high prices replacing vice.

5. Bard College: A Crucible of Counterculture and Collaboration

On a dark, drizzly morning, the first day of school, my father and I loaded up the trunk of his Olds Dynamic 88 in preparation for the drive to upstate New York.

Escape to a progressive school. Bard College, known for its progressive nature, attracted a diverse mix of students, including suburban misfits like the author. The move represented an escape from the perceived conformity of suburban life, despite the initial shock of the dilapidated dorms.

Psychedelic experiences. The college years coincided with the rise of the counterculture and psychedelic drugs. The author's first LSD trip, guided by Timothy Leary's The Psychedelic Experience, was a profound, ego-dissolving event. Later, experimenting with DMT and marijuana was part of the campus scene, though it also led to anxiety attacks.

Meeting Walter Becker. A pivotal moment was meeting Walter Becker, a fellow student with a shared passion for jazz, blues, popular music, and "black humor" literature. Their collaboration began in a small sitting room, bouncing "clowny ideas" around and developing a unique musical and lyrical sensibility that would define their future work.

6. The Music Business and the Reality of Touring

Fast-forward to 1988. (Please!) I was feeling a lot better.

From studio to stage. After initial struggles as staff songwriters, the author and Walter Becker found success with Steely Dan, leading to a career that eventually involved extensive touring, a different beast from studio work. The Dukes of September Rhythm Revue tour provided a new context for experiencing life on the road.

The grind of the road. Touring life, even with some amenities, is depicted as a physically and psychologically taxing experience, marked by:

• Constant travel and lack of routine
• Uncomfortable hotels and venues
• Difficulty maintaining health and well-being
• The pressure of nightly performance

The artist as commodity. The touring journal highlights the commercial realities of the music business, from venue sizes dictated by market profile to the disconnect between the artist's creative intent and the audience's expectations, particularly with "TV Babies" who primarily want familiar hits.

7. Aging, Anxiety, and the Changing Cultural Landscape

Okay, that’s it. Not even three weeks out and I’m starting to crumble.

Acute Tour Disorder. The physical and mental toll of touring exacerbates the author's existing anxieties and vulnerabilities, leading to symptoms he labels "Acute Tour Disorder," including insomnia, paranoia, and depression. The stress of performance, seen as a "ritual slaying," is exhausting.

Cultural observations. The touring experience provides a platform for observations on contemporary American culture, including:

• The prevalence of "Plasticulture" and simulation
• The impact of television on younger generations ("TV Babies")
• The perceived mental illness of right-wingers ("amygdala thing")
• The decline of authentic cultural experiences

Facing mortality. The journal is punctuated by reflections on aging, loss, and mortality, including the tragic death of his wife's son and his own health anxieties. These personal struggles are interwoven with his observations on the broader cultural decline.

8. Reflections on Hipsters, Authenticity, and Decline

There are countless definitions of the word “hipster.”

Defining the hipster. The author uses "hipster" to refer to artists originating outside the mainstream, creatively exploiting marginal material, or seeing truth from a "freaky space." His early influences, like the Boswells and Mancini, fit this definition, as did figures like Jean Shepherd.

The quest for authenticity. Throughout his life, the author has sought authenticity in music and culture, often finding it in figures who operated outside the commercial mainstream or subverted it from within. This quest is contrasted with the perceived inauthenticity and "Big Stupid" of contemporary culture, exacerbated by technology and mass media.

A world transformed. The book reflects on the vast changes from the author's youth to the present, lamenting the loss of certain cultural touchstones and the rise of a simulation-based reality. Despite the challenges of aging and the road, the power of great music and genuine human connection remains a source of value.

Last updated: May 6, 2025