Having lived in Manhattan for about twenty years, I’ve had my fair share of “encounters” with celebrities.

Many famous people -- singers, actors, politicians, athletes, etc. -- live in New York or visit here quite frequently, given that the metropolis is a global center for media, art, fashion, cuisine and finance.

In the beginning, seeing celebrities in the flesh was an exciting and exhilarating experience. However, as the years passed, I became more of a proverbial “jaded New Yorker” and realized that it was a routine thing to observe people who have been blessed (and, in some cases, plagued) by fame, wealth and celebrity.

As a result, I have seen or run into literally hundreds of celebrities -- ranging from global icons to the Andy Warhol ‘fifteen-minute’ variety -- in Manhattan over the past two decades.

Here are some general observations I have made about such celebrity sightings/encounters:

*Celebrities generally don’t like being noticed or bothered; they (quite understandably) just want to live their lives in peace.

*Most celebrities look worse in 'real-life' than they do in the newspapers or on TV and films. Typically, they are shorter, heavier and less attractive than you would imagine – indeed, make-up and studio lighting can do wonders for one’s pulchritude).

*Although most celebrities want to be left alone, they concurrently want to enjoy the perks of fame and privilege (that is, they can’t stand waiting in lines or waiting too long for a cab, etc.).

*Most celebrities are ‘normal people’ who cannot believe their good luck and actually want to try to live as ordinary a life as possible.

I would imagine that New York – since it’s so small, concentrated, and densely populated – is a better place to star-gaze than Los Angeles, where the car/driving culture imposes more of a barrier between the famous and the rest of us.

Plus, I make a distinction between an “authentic” celebrity encounter, versus an “artificial” one. What I mean by that is that if one hangs around long enough at Sixth Avenue and 51st Street, near Radio City Music Hall, NBC Studios etc., one will undoubtedly happen to catch a number of famous people who are coming and going from TV interviews or what-not. To me, a “genuine” celebrity encounter is one what happens during the ordinary course of one’s day – in an unexpected manner.

There is also another dimension to this discussion – the quality of fame.

That is, one must examine exactly what “fame” means in this contemporary era of tabloid/trash TV, internet and instant messaging.

There are those few special souls whose fame is based on extraordinary accomplishment and whose celebrity will likely last forever (Frank Sinatra, Beatles, Elvis Presley, Bing Crosby, Woody Allen, Michael Jordan, Albert Einstein, Steve Jobs, etc.). In the next level down, there are those celebrities who happen to either belong to the ‘right’ family or happened to be at the right place at the right time (most of the Kennedy family, etc.).

Then, in the lowest rung of celebrity are those souls who are famous for no conceivable reason whatsoever; that is, they have no talent, no skills, virtually no redeemable characteristics at all (Kardashians, Paris Hilton, etc.)

Conversely, I think the relationship between ‘celebrity’ and ‘ordinary fan’ has dramatically changed over the past decade or two.

As the concept of ‘fame’ has been diluted, cheapened and degraded, many, many non-famous people now believe that they, too, are celebrities – or, at least, they act and dress like it. I’m sure you have seen such folks – there are literally thousands of them in New York alone. They may work as secretaries, administrative assistants, nurses, bureaucrats, etc., by day, but they have deluded themselves into thinking they are celebrities (despite the fact that they enjoy no fame whatsoever).

They pretend that they rub elbows with the glitterati, have the same lifestyles and concerns as genuine celebs, and “look down” upon us ordinary folk.

In a way, I don’t blame them. I mean, if Kim Kardashian is famous, than anyone can be.

Along these lines, I have a friend (a middle-aged man who does not live in New York) who is absolutely obsessed with the dying art of rock-and-roll music. He possesses thousands of vinyl albums (and now CDs), and has attended hundreds of concerts over the past 30 years. He still wears his hair long (what he has left of it), wears T-shirts featuring concert tours from days gone by, and has long indulged in drugs and alcohol (in pale imitation of his rock star idols).

In reality, he has a mundane, lower middle-class life in a small nowhere town – but he has embroidered a complex ‘fantasy world’ in which he thinks he is part of the ‘rock-and-roll industry.’

Moreover, his delusions are so deeply-entrenched that he seems to think that rock stars (whom he has never even met) are his close, personal ‘friends.’ He even refers to them – dead or alive – by their first names (“Mick,” “Keith,” “Jimi,” “Bruce,” etc…)

Clearly, my friend lives vicariously through wealthy celebrities in order to fulfill some deep emptiness in his soul. I used to think he was a unique, singular case – but now I realize there are many people afflicted with this same ‘disease.’

A sidebar to this discussion is the rise of tech billionaires who in the past decade have soared to the very top of celebrity-dom. Bill Gates, Mark Zuckerberg, Larry Page, Sergey Brin, and the recently departed Steve Jobs have attained the zenith of fame (as well as income no one’s ever seen before). However, these tech ‘nerds’ and ‘geeks’ are unlike any kind of celebrity from previous generations.

Despite their vast wealth and global acclaim, they generally lack the glamour, good looks and scandals we associate with ‘conventional’ paparazzi.

It makes me wonder – when Bill Gates strolls down the street, do people gasp and scream? Do they run to him begging for autographs? Or do they ignore him since he seems like a rather dull, drab and uninteresting person?

In any case, here is a sampling of some more of my ‘celebrity encounters’ in New York:

Woody Allen: As a teenager and in my early 20s I was a devoted and enthusiastic fan of Woody Allen’s brilliant, acerbic comedy and films. However, as I got older I gradually lost my enthusiasm for him and don’t really bother keeping track of him anymore. (I think most people do this in reverse – that is, as teens they like silly, tacky comedies and gradually move onto more sophisticated fare like what Woody offers).

No matter, one summer weekend afternoon a few years ago as I was strolling near 5th Avenue on the Upper East Side of Manhattan, I saw the great man sitting on a bench next to the Jewish Museum. He was (bizarrely) wearing what looked like a sailor’s cap and a rather rumpled shirt and pants. I think he was accompanied by his Korean wife (or is she his step-daughter?).
I was struck by two things: how incredibly homely he was; and by the fact that if you didn’t know who he was, you’d think he was biggest loser on earth. And yet, he is one of the most respected and admired filmmakers on the planet and a genuine global icon.
I figured he dislikes fans (and the public at large), so I strolled by without saying anything or even acknowledging him (very ‘New York’).
One more thing about Woody – he’s not quite the “pure artist” he claims to be. Despite his image of shunning Hollywood and focusing purely on his “art”, he, too, is concerned about money. Many years ago when I was in Japan I was watching TV when I saw Woody on a commercial hawking some product. I was stunned – how could he, of all people, succumb to such crass commercialism? I learned later that Woody generated a lot of revenue by appearing in promotions and commercials in a number of foreign countries (that is, far from his core audience in the U.S. who would likely be appalled by such ventures).

David Bowie: When I was a child, David Bowie – in the guise of ‘Ziggy Stardust’ and the ‘Thin White Duke’ and other fanciful characters – was the biggest pop star in the world. He was so huge and popular that (as I recall), some critics believed he could supplant The Beatles in terms global fame and influence. Well, that didn’t actually happen, but Bowie has indeed carved out an extraordinary and stellar career.

I had read somewhere that he lived in downtown Manhattan part of the year, but I never dreamt I would ever see him in person – until, one afternoon I was sitting in an outdoor restaurant in Soho. I first spotted this little man across the street wearing an army fatigue jacket (despite the warm weather) and blue jeans, He also wore dark glasses and was carrying a rather large camera, hanging from his neck. He looked terribly familiar, but I couldn’t tell who it was.

Lo and behold, he crossed the street near to our locale -- I was flabbergasted to see that it was none other than David Bowie.

He was probably about 50 years old at that time but he looked exceptionally young, with a handsome face, sharp features and those unforgettable mismatched eyes.

But…. he was so short. He couldn’t have been more than 5-foot-5 or so. Having never seen him before in person, I was shocked and distressed by his tiny size. Perhaps I am biased against short people, but I couldn’t fathom how someone so small could dominate the merciless pop culture market for three decades.

He seemed like a nice fellow, though, and also appeared to acknowledge my persistent stare.

I read somewhere later that Bowie (a true renaissance man) spends a lot time photographing industrial sites of cities on his own time and frequently walks around in public in this pursuit. His “image” was indeed correct -- he really is an eccentric.

Lou Reed: One evening in the early 1990s as I boarded a subway in downtown Manhattan after a night out on the town. I noticed a strange man getting in the car at the Bleecker Street station. His face was tan and weathered and his clothes seemed awfully tight and inappropriate for someone of middle-age.

Lou Reed is a rock-and-roll icon, but this evening, he was just another hapless commuter on New York’s dreary mass transit system. He had a cold, hard look on his face and he clearly was in no mood for chit-chat. But that was okay, since I was not such a big fan of his anyway, although I liked some songs recorded by his immortal group, The Velvet Underground.

Nonetheless, I was amazed that a rock star would actually ride the subway like an ordinary person – I just couldn’t imagine Mick Jagger doing something like that.

He got off a few stops later and it occurred to me that some famous people want nothing whatsoever to do with the trappings of celebrity – and thus I’ve admired Reed ever since.

James Gandolfini: As a great admirer of ‘The Sopranos’ television show, I knew that the program was filmed in the New York area and most of the stars lived and hung around the city. Still, that did not adequately prepare me for the sight of James Gandolfini sitting outside a café in the East Village a few years ago (when the show was still active, I think).

But this was not Tony Soprano, the finely-tailored mafia boss and harried suburban New Jersey father and husband – rather, this was the ‘real’ Gandolfini, with a moustache, scruffy beard and wearing what looked like a caftan (i.e., he displayed himself in a way that Tony never would in a million years).

He was sitting down (attended by a young man whom I assume was his bodyguard) and speaking into a cellphone. I could tell he was physically huge, with a tremendous girth.

Even though I’m a (reasonably) mature adult who understands that films and TV shows are ‘make-believe,’ I nonetheless felt intimidated being anywhere near Tony Soprano, er, I mean, James Gandolfini.

I said nothing to him – what would one say to Tony Soprano?

However, I liked the fact that a great many actors prefer to live in New York rather than Los Angeles, despite the terrible weather here.

Jackie Kennedy Onassis: I must insert a qualifier here – I’m not exactly certain I saw Jackie, rather I THINK I saw her. It was in the early 1990s as I strolled down Fifth Avenue, I saw this elegant older woman wearing sunglasses walking towards Central Park.
She certainly looked like Jackie (at one time the most famous woman on the planet) and I was intrigued. She was completely alone. I must admit, I wanted badly to speak to her, but it didn’t seem at all proper. I’d feel really silly if it wasn’t her.

Although I have no admiration or fascination for the so-called ‘Kennedy mystique’, I have always liked Jackie and admired her beauty.

Why is she famous? Because she married two of the most famous men on the planet and she is widely viewed as a tragic figure – she really did not ‘accomplish’ anything to ‘earn’ her fame.

But I can overlook this since I was so impressed by her style, restraint and refusal to submit to the paparazzi.

After Jackie died, I read that while living on 5th Avenue, she often strolled in the park. I’d like to think I did indeed see Jackie.

Some celebrity sightings are far more satisfying than others.