I think what would be perfect would be following a road player level pool player through an entire lifetime of pool. The character could be finctional, and then have that character come into contact with many well known players of many era's.
If you ever read the book McGoorty, that is the type of story but start it in the 1950's.
Some 16 year old kid from New York or the like. Have him starting out in the pool hall, dropped out of school, watching the local talent and slowly learning at a nickle a game while working as a gas jockey to get that money he looses week after week. Quick scenes, the kid has a knack for the game and gets better fast.
Still has his heroes, that are yacked about in voiceover Goodfella's style "Little Joe, now THAT guy was a player, smooth as silk, noone in Junior's messed with him. Until one day." Show the road player coming in with his buddy or two, a recollection by the kid of a match that suddenly took place, phone calls flying out to backers, people crowding into the pool hall, some richer men with cash to put up on Little Joe, side action on the rail like crazy, and a battle for the cash that lasts hours.
With the voiceover still going we get the short version "We were all there to watch Little Joe take this guy down, he had no idea what he was getting into. Only, it seems he did. Little Joe shot good, better then I had seen him play. He was more focused, he was more methodical, he was shooting great. But he was losing. This guy playing Little Joe was flat out better. Little Joe had always seemed untouchable, every time you missed in a game against Little Joe it would cost you 50 points on average, only when Little Joe then missed back this guy would up and run 80 back. Once the dust settled Little Joe had lost, the whole of Juniors had lost close to $2,000 total. The next day in the pool room a few people talked about the match, some people were playing for nickles in the back corner, and Little Joe was sitting in his usual chair at bar drinking his usual coffee. It was like it had hardly happend, but it had, and I wanted to see more."
So the kid now 17 or 18 or so starts hitting other pool halls, we get the voiceover of the places he hits (famous pool halls of New York 101), hear about his rise in ability and starting to become one of the better and known players in New York, eventually even reaching the level of Little Joe, and realizing that there are many levels above when he gets the chance to watch the World Straight Pool Championships in New York with Ponzi, Caras, Crane, and last but not least Mosconi who wins the event for that year and leaves our lead character in awe.
And so, having pretty much become known in New York and getting only able to get action against the guys he cannot beat he hits the road with a buddy of his, also a player but not quite as good and with a screw loose and a knack for getting into trouble and loosing money on bad bets. We get a few scenes and moments of this early time on the road, some of the players, some of the scores, some of the loses, some of the women, some of the trouble. Eventually shit hits the proverbial fan and our lead character has to cut loose from his partner, we get the short voiceover version of what became of him.
And so on, through the ages, as the player matures from a 1950's greaser era kid as he finds the game and learns to become a decent player, following him across the USA on a backdrop of the 1960's hippy culture as he is now a young road player hitting all the various areas of the country, learning where to play, where not to play, and learning that the relatively new game of 9-ball is slowly taking over from Straight Pool. Follow him into the 1970's, now a older and more knowledgable player far more able to assess situations, far better known, now often when he enters a pool hall he is recognized, sometimes with a covert nod from a fellow player, sometimes with a laugh from the local champ who might have played had he not watched our character play "Pistol Pete" back in 68' in Missouri. We watch the world changing still, the 60's are over, the scene begins to shift, the musical background of the movie changes, the players change, the tournament scene starts to become more important. Move to the 1980's, our character now getting older, still shoots good but the scene is different now, the action of old times is almost gone.
And into the 1990's, our character now a older gentleman sitting in a pool hall watching some younger "kids" shooting pool, decent players, one might have a chance of making something. The whole pool scene now going international, the TV is showing a replay of the World 9-ball Championships, the players are a far cry from the players that the main character once knew as he remenices about past friends, competitors.
This type of movie would mostly be made up of alot of short scenes and happenings that help define the pool scene and the character just happens to be a part of. An example would be the story from Di'Leberto's book with Lassiter and the girl he liked. Pool matches such as took place in "Playing off the Rail". The Jansco Brother's tournaments. ect...
And all in the style of a trip through time much like Goodfella's with voiceover and the main character kind of leading teh journey much like Ray Liota did in that flick. Special detaill to the era's, like a trip through history, using the music of the era and the place. AKA when the character first hits California, driving down the road along the beach with the Beach Boys or California Sun by the Rivieras on the radio. You need to play to stuff like this.