In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.

Hollywood careers are full of make-or-break moments. For Clint Eastwood, one such moment came when studio powers agreed to let him make his directing debut. That story and others comprise this portrait of the famed Hollywood icon. His career is explored via an array of film clips, interviews and more.

The outrageous, groundbreaking comic Lenny Bruce, whose iconoclastic material in a conservative era got him into tragic trouble, is profiled by a close friend, Fred Baker, who prefers to remember the laughs Lenny Bruce's memory evokes instead of the tears. By presenting Bruce's landmark skits on the Steve Allen Show, his failed TV pilot episode and a candid interview with Nat Hentoff, Bruce's genius and anguish show through the dramatic and tragic trajectory of his career from aspiring artist to hunted "lawbreaker".

'Pleasures' profiles legendary jazz critic and civil libertarian Nat Hentoff, whose pioneering career tracks the greatest cultural and political movements of the last 65 years. The film is about an idea as well as a man - the idea of free expression as the defining characteristic of the individual. Hentoff is a pioneering journalist who raised jazz as an art form and was present at the creation of 'alternative' journalism. 'Pleasures' wraps the themes of liberty and identity around a historical narrative that stretches from the Great Depression to the Patriot Act. With a mix of interviews, archival footage and music, it employs a complex non-linear structure to engage the audience in a life of independent ideas and the creation of an enduring voice.

Renowned journalist and jazz critic Nat Hentoff tells the story of his longtime colleague, pioneering TV writer/director/producer, Robert Herridge. Herridge, working closely with Hentoff, was the key force behind the making of some of the most important music productions in American television history, from "The Sound of Jazz" (1957), featuring Billie Holiday, Thelonius Monk, Lester Young, Count Basie, Coleman Hawkins and Roy Eldridge, to "The Sound of Miles Davis" (1959), with Davis, John Coltrane and Gil Evans ... to a pair of folk and blues shows, featuring Joan Baez's first national TV appearances (1960), which Bob Dylan says enticed the then 19-year-old Minnesotan to move to New York City and begin his extraordinary career. "The Jazz Television of Robert Herridge" offers Nat Hentoff's video-rich celebration of one of the great musical collaborations of the 20th century.