Bourgeois Bohemian

The Bourgeois Bohemian is often what the Hipster or Granola Girl turns into when he/she hits middle age, or what the New Age Retro Hippie might have become had he not dropped out.

The defining trait of the Bourgeois Bohemian (Bobo for short) is that while he belongs to the upper or upper-middle class in economic terms, his values are inherited from the countercultural movements of the 1960s. Expect very open attitudes towards issues such as sexuality and recreational drugs, support for liberal/progressive political causes, and possibly some hypocrisy as well. And definitely a fondness for NPR and PBS. Unsympathetic examples of the trope will often be portrayed as hypocritical about their wealth, criticizing other wealthy elites while sharing much of their lifestyle. "Limousine liberal" (US term) or "Chardonnay socialist" (UK term) are some pejorative terms you'll sometimes find applied to this type. Sympathetic portrayals will usually not suggest that anything is wrong or contradictory about liberal ideals coupled with financial success.

When they show up in fiction, it is often as a main character's Hippie Parents, and they are very likely to live in San Francisco, since that city is known both for being very liberal and for having a very high cost of living.

See also: The Man Is Sticking It to the Man, Rule-Abiding Rebel, and Upper Class Twit. If the aging character loses the values themselves as well as the trappings thereof, they become a Former Teen Rebel.

Examples of Bourgeois Bohemian include:

Comic Books

Underground Comics artist Mary Fleener met some of these people. Like an ex-hippie girl turned stereotype yuppie, and a former (female) drug dealer who became a realtor.

Film

Greg's parents in Meet the Fockers.
Tanguy's parents.
The protagonists of Mammoth, a 2009 film by Lukas Moodyson.
Ben Stiller's real parents in Flirting With Disaster, played by Alan Alda and Lily Tomlin.
Jane in 2009's It's Complicated, though her ex-husband seems to be more of the businessman type.
Olive's parents in Easy A.
Everybody in The Big Chill.
Team America: World Police casts a number of Hollywood celebrities as wealthy liberal activists who try to aid Kim Jong-Il.
Varying degrees in the main characters in The Decline of the American Empire and The Barbarian Invasions, by Quebecois director Denys Arcand.

Literature

The protagonist's parents in The Elegance of the Hedgehog.
The protagonists of Freedom by Jonathan Franzen.
Discussed and critiqued in the non-fiction book The Rebel Sell as part of the shifting values of the political left from old-school socialism to counterculture hipsterism, and how these values have fed the consumer culture they claim to resent.
Similarly discussed in Thomas Frank's 2004 book What's the Matter with Kansas: How Conservatives Won the Heart of America. He charges that many of the U.S. political class's wealthy leftists are not really leftists at all; they are "libertarian" (which in American political parlance roughly equals "moderate conservative") opportunists who feign politically correct attitudes in order to appeal to more upscale (and ostensibly more sophisticated) urban and suburban voters in the "blue states". Conversely, those elites who live in the "red states" generally prefer to act like right-wing culture warriors in order to court the more downscale (and generally more traditionalist) constituents of America's conservative coalition.
1632: Thomas "Stoner" Stone is a last-wave hippie, whose knowledge of chemistry (he made LSD in the sixties) has made him one of the richest men in Europe, with a personal fortune that rivals that of many nations. He is completely devoted to the ideals of peace, love and understanding, in word and deed. For example, he refuses payment for all medicines he makes, only making money from dyes and cosmetics. Profiting from people's vanity is OK, profiting from their pain is not.

Live-Action TV

Family Ties, which is centered around the conflicts between Bobo parents and their Reaganite conservative offspring.
thirtysomething also lives for this trope.
Dharma's parents in Dharma and Greg.
Paul Kinsey on Mad Men is the Beatnik version.
Portlandia makes fun of the suburban counter-culture scene of Portland, Oregon. Many characters are middle-aged professionals with bohemian values.
You could also definitely include Warren and Lois Whelan—Debra's wealthy (or at least upper middle-class) parents—from Everybody Loves Raymond. When they first appear, Ray, Frank, and Marie are not looking forward to it, groaning about how much Warren and Lois basically embody this trope to a tee, and how different their own blue-collar family is from the Whelans. When they arrive later in the episode, Hilarity Ensues obviously. Over the course of the series, Warren and Lois continue to embody this trope, leading to more awkwardness (and hilarity) when they and the Barones interact.
George in Bored to Death, played by Ted Danson, is a pot-smoking hippy who manages a magazine similar to The New Yorker. He's quite wealthy, but still has his left-wing lifestyle and opinions. In the second season, he suffers a serious clash of cultures when his magazine is bought out by a right-wing organization.

Music

This sort of character is referenced in Don Henley's haunting hit song "The Boys of Summer", which is about aging and looking back at the past. The particularly poignant line "saw a Deadhead sticker on a Cadillac" paints a harsh image of contrast: the Grateful Dead represented a freewheeling lifestyle (they openly encouraged bootlegging and it is a large part of Deadhead culture), while Cadillacs are expensive and images of luxury and social status. The Ataris cover changes the sticker to Black Flag, which is ironic conisdering that Black Flag singer Henry Rollins now pitches for Infiniti.
Barbra Streisand is often seen this way.
Henry Rollins is a punk rock icon who now regularly gives spoken-word performances from his liberal point of view. He's obviously made quite a lot of money over the years from his music, acting roles and voice-over gigs. He's now the voice of Infiniti luxury automobiles.

Web Comics

Mildred's parents in Bad Machinery.

Web Original

Stuff White People Like is generally written from a metropolitan, bicoastal, college-educated, liberal point of view, which would include a lot of Bourgeois Bohemian tastes.

Western Animation

Though he's technically part of a blue-collar household, Brian Griffin of Family Guy has most of the stereotypical traits of this type, up to and including driving a Toyota Prius.
Bessie's mother in The Mighty B!.
Munchie and Seth in The Simpsons episode "D'oh-in in the Wind."
In the South Park episode "Smug Alert", the adult residents of San Francisco are portrayed as bourgeois bohemians who are so smug and self-satisfied that they enjoy the smell of their own farts.

Real Life

New York Times columnist and PBS/NPR correspondent David Brooks coined the term "Bourgeois Bohemian" in his book Bobos in Paradise...and actually admits in the book's introduction that he himself probably counts as one.
Celebrities in the entertainment industry are often Bourgeois Bohemians, probably due to their combination of wealth and liberal arts backgrounds.
- Movie stars such as George Clooney, Dustin Hoffman Sean Penn, Ben Affleck, Alec Baldwin and Eva Longoria are notable examples of celebrities who stump for liberal causes.
- Critics of Michael Moore point out that while he makes documentaries that criticize big business and support working class families, he is himself wealthy and sent his kids to private school.
- Examples in the music industry include Barbra Streisand and Neil Portnow, head of NARAS (which gives the Grammy Awards), who once used his annual address at the Grammys to editorialize on the Iraq War.
  - Trey Parker and Matt Stone have often mocked Hollywood and the music industry for their tendency to embody this trope, usually in South Park with Mecha-Barbra Streisand and George Clooney's "Cloud of Smug" being prime examples from the show, but also in other works like Team America: World Police. In a 2004 interview, creators Trey Parker and Matt Stone remarked that "People in the entertainment industry are by and large whore-chasing drug-addicted fuckups...But they still believe they're better than the guy in Wyoming who really loves his wife and takes care of his kids and is a good, outstanding, wholesome person. Hollywood views regular people as children, and they think they're the smart ones who need to tell the idiots out there how to be." Parker and Stone also continued this theme in the movie Team America: World Police, in which several celebrities foolishly support Kim Jong Il.
In addition to San Francisco, places in the U.S. likely to be considered havens for these types of people include Boston, Massachusetts (and the nearby suburbs of Cambridge and Brookline); Seattle, Washington; Portland, Oregon; Boulder, Colorado; Madison, Wisconsin; Ann Arbor, Michigan; Park City, Utah; and, over the past decade, Hoboken and the downtown section of Jersey City, New Jersey. And, obviously, New York. Washington, D.C., and northern Virginia are inevitably seen as having both these (as well as plenty of Republicans running around, although more so in northern Virginia than in New York).
Hipsters, especially younger and more suburban ones, are generally seen as a junior version of the trope. Teens and especially college kids who espouse strongly liberal, counterculture and anti-establishment views are often criticized for doing so from a position of material comfort, being supported by their parents and lacking experience in the "real world."
In Britain, there are certain things that are associated with this trope. Generally people who live in Islington are seen as an example and the word Islington itself is synonymous with this sort of stereotype. Also, people who read the upmarket left-wing paper The Guardian are also seen being this.