OK, so there are several problems with this 1998, sensationalist tale of Sinatra, his cronies, JFK and the mob. But, flawed as it may be, there is enough here to make it worth watching.
The major issue is the fact that Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, JFK, RFK, etc., etc. were so visible on screen back in the day and their images are forever preserved in peoples minds and memories forever. So when one sees a film like this, and they see contemporary actors playing historical figures of just a few decades ago, it doesn't always sit well with the viewer. Right off the bat, the cards were stacked against this film. Hell, in that respect it would be easier to make a film about Helen of Troy than Ol' Blue Eyes (We don't know for sure what she looked like, but we know she was attractive enough to launcha thousand ships).
The other issue was that Sinatra himself and his people tried desperately to a put a stop to this film. This is rather odd. Though he's hardly portrayed in the most positive light, he comes across much better here than he did in the 1992 miniseries which was authorized by Sinatra and produced by his daughter. Odd. At least here, Sinatra is seen as being someone who would do anything and everything for his friends.
Really, the plot focuses on Frank and the boys having the time of their lives as they quickly come together, film "Oceans Eleven," help elect Kennedy, and live large. Though their peak lasts only so long, it sure looked like a lot of fun.
Ray Liotta does a great job as the Chairman of the Board. He perfecty captures Sinatra's erratic behavior, volatile personality and borderline manic-depressive personality. He may seem, to some, like an odd choice, but check him out. You will be impressed.
Joe Mantegna tries his best to capture the essence of Dean Martin- an impossible task. While he looks and talks the part quite well, he never seems fully at ease in the role. Still, one must applaud his effort. Not even those closest to Dino knew him that well, so it can't be easy for any actor to truly get inside this enigmatic character.
Don Cheadle is quite good as Davis. Davis' voice and gestures have been so mocked over the years that it would be easy to play this character as a total caricature, but Cheadle brings tremendous heart to this role.
Speaking of caricatures, check out the Kennedy brothers! They may look the parts, but the actors are far from convincing (especially their awful faux-Boston accents).
Perhaps the real find here is Angus MacFayden as Peter Lawford. Not does he only bare a striking resemblance to him, but MacFayden seems to embody this troubled and tragic figure perfectly (Lawford was Sinatra's liason to JFK). His final confrontation with Liotta, at the very end of the film, is explosive and well worth the wait.
Critics may have reached their vedict prematurely on this film, claiming it to be a travesty and a poor depiction of somebody who is regarded as Hollywood royalty. At the end of the day, though, it is just a film and an entertaining one at that. It won't erase your memories of these pop-culture icons, but it will sure make you look at them from a different persepctive.