For several years in the 90's, I bought a couple of dozen music magazines per year, both weeklies and monthlies. The NME/Melody Maker/Select style was a fly on the wall approach. The journalist would join the artist or band in their natural environment (in the studio, on tour, their favourite pub, whatever the case may be), soak up the atmosphere, and grab as many juicy quotes as they could. The Canadian free weeklies and monthlies (NOW, eye, Exclaim!) used a more measured style, it was rare to see a circus-type presentation, the interviews were more straightforward reporting. This isn't necessarily a negative, but the British style was more consistently entertaining. But of course, the free magazines didn't do long form highly in depth articles, their format limited the space they could afford for any one story compared with the paid publications.
This is all to say that the style of the Playboy interview -- a long form, deep one-on-one conversation without any of the scenic bells and whistles -- is rather new to me. The list of names (all of them men) is stellar, but when it misses, it really misses, and the conversation bogs down in dreadful minutiae and elongated tedium. It's like reading the transcript between a reluctant host and hangers on at a party who simply refuse to leave. The Bob Dylan interview (March 1978) is an unfortunate example of that. David Bowie (September 1976) says very little of substance, and Elton John (January 1976) dances around nearly every serious question aimed at providing genuine insight into his thoughts, in particular, his thoughts on homosexuality and bisexuality (understandably so, considering the time, but it doesn't make for entertaining reading). Luciano Pavarotti (November 1982) is a unique look at a personality that was never featured in "rock" mags, but the conversation is just too damned long, stitched together from multiple conversations.
I want to lump together three interviews from the 90's, which carry similar goals but produce wildly varying results. The idea is to interview a living legend, reflect on his career, celebrate his accomplishments, and speculate on their continued relevance into the 90's. Berry Gordy (August 1995) comes across like a complete asshole, defending his policy of indentured servitude for his artists in the 60's and generally showing himself to be out of touch with most music and artist relations post-early career Michael Jackson. Frank Zappa (April 1993) is as unfiltered as you'd expect. His fans (I was never one) would probably enjoy his wild musings on politics and parenthood, he was undoubtedly one of a kind but if you never acquired a taste for his music, the interview probably won't be to your liking either. He also speaks openly about his health, and would sadly pass away less than a year following the interview. Pete Townshend (February 1994) owns up to all his problems past and present, he's a real person prone to temper tantrums, bad decisions, and frequent vacillations in opinion. Compared to the David Bowie and Elton John interviews from the 70's, where they were ultra-careful in protecting their image and not harming their marketability, Townshend is firmly in give no fucks mode.
The most recent interviews with Jay-Z (April 2003) and Kanye West (March 2006) encapsulate the rapid decline of the print mag industry. In the 21st century, the 24/7 news cycle was an essential service, the internet was in every household, and the rapid rise of social media was just around the corner. Fans no longer needed these types of interviews to gain rare insight into musical giants. Jay-Z is entertaining and larger than life, but the interview is nothing special, he's punching the clock and not revealing anything about his true self. On the other hand, Kanye gives clear glimpses of what he eventually became fifteen years later, speaking openly about his pr0n addiction and attraction to conspiracy theories.
The highlights are the first three interviews in the collection. They're like a time capsule into a long ago era of life in America. Frank Sinatra (February 1963) is politically incorrect, boorish, and arrogant, but you can't say he didn't show up ready to play ball. He gives his unfiltered opinion on politics and foreign affairs, providing views that were far from mainstream. He's determined to advertise himself as as a thinking man's performer who wouldn't stand for any politician's bullshit, and couldn't care less if he comes across as a "difficult" interviewee. The Beatles (February 1965) are immature kids captured at the height of their teenybopper fame. Before they retired to the studio, took drug-fueled trips to India, and became peace crusaders, there was this, just four young men riding a pop star wave the world had never seen. Some of their comments have not aged well, but it's refreshing to read something of this length about the Beatles that was published before the legend was complete. Best of all is the interview with Ray Charles (March 1970) who comes off as the most intelligent man in the country, a musical prophet who speaks candidly and impactfully about US race relations and his niche as a performer.