In High Fidelity, Dick, Barry, and Rob are like one of their friends says, Under-appreciated Elitist Snobs. They are anachronisms stuck in the past (their rock n' roll youths), still listening to outdated music on records, still wearing vintage clothing and Cosby sweaters, and hoping, *HOPING* to start a band, produce a group, date a rock star, or at least have a rock star mention them in an album's liner notes.
Like some veterans who never got over 'Nam or their band opening for Nirvana, Dick, Barry, and Rob never got over their love affair with 70s rock and roll. As Rob says:
I get by because of the people who make a special effort to shop here on Saturday young men, always young men, who spend a disproportionate amount of their time looking for deleted Smiths singles and "original not rereleased" underline Frank Zappa albums...The fetish properties are not unlike porn. I would feel guilty taking their money if I wasn't, kind of, well, one of them.
As Rob's girlfriend says, Rob takes pride in the fact that he has never "sold out," which is an excuse really for never having to change or grow up or commit to anything like a relationship, marriage, or kids. Rob is jealous that his girlfriend has cut her hair, gotten a job, and grown out of her rave dancing days.
As for Dick and Barry, they are the comic relief, polar opposite foils of non-responsibility. Barry is the harsh critic, the id, full of bombast and overstatement. Dick refuses to be a critic at all; he is the superego, full of deference and shame. Together, they foil Rob because they, unlike him, do not have a top 5 list of breakups. They'll be lucky to land a girlfriend at all.