Set during voting in the 1968 California presidential primary, Bobby is populated by two dozen focal characters who move in and out of the Ambassador on the day the senator is shot. Kennedy's campaign headquarters are in the upper floors of the hotel, and campaign workers assemble in the plaza outside its front doors. John (Anthony Hopkins), the hotel's doorman for three decades, holds court in the lobby and plays chess with old friend Nelson (Harry Belafonte), another retired hotel employee. Busboy Jose (Freddy Rodriguez) has been assigned a double shift because of the campaign celebration that will follow dinner. He's upset because he has tickets to take his father to Dodger Stadium where Don Drysdale hopes to set a pitching record.
Lounge singer Virginia (Demi Moore) gets drunk in her suite while her manager/husband Tim (Estevez) contemplates leaving her. Wealthy Kennedy fans Jack (Martin Sheen) and Samantha (Helen Hunt) have traveled from New York to be present at the party for the victory they hope will seal the Democratic nomination for their hero. College student Diane (Lindsay Lohan) gets a manicure while waiting for the hotel's serially booked chapel to clear for her marriage to Will (Elijah Wood). The bride and groom aren't in love and seem barely to know each other. They are marrying to protect him from being sent to Vietnam. Devout Kennedy supporter and hotel manager Paul (William H. Macy) has such strong feelings about racial justice that he fires his food manager Daryl (Christian Slater) for making disparaging remarks about the black and Hispanic men who work for him. Paul's liberal attitudes don't extend to women, however, as his wife (Sharon Stone) knows. Moreover, Paul is a philanderer, who has been sneaking into empty rooms for "nooners" with hotel telephone operator Angela (Heather Graham). All this menagerie of human beings from different classes, races and cultures find themselves gathered in a small, tight space when the world-changing shots ring out.
Interestingly, Estevez evinces no interest in the continuing controversy about who actually shot Robert Kennedy. No one disputes that Sirhan Sirhan fired eight shots from his .22 revolver. But many dispute that even one of Sirhan's bullets hit the senator, whose body and clothing was struck four times. Nor, aside from stirring campaign footage showing the candidate mobbed by admirers, does Estevez endeavor to reveal the basis for Kennedy's appeal. The movie is about the varied and complicated lives of its fictional characters, not about a remarkable political figure extensively reinventing himself in a campaign that imagined America in a daring new way. Bobby takes its titular character for granted, an established liberal icon for the likes of people like me. And that's the filmmaker's privilege. Other films can look at Kennedy's life and the astonishing transformation he underwent from Joe McCarthy staffer to spokesman for the nation's poor and underprivileged. This one looks instead at a cross section of the nation Kennedy sought to lead and very probably would have led had he lived.
Estevez clearly renders each character as a type: a draft dodger, an idealist, an illegal alien, an abused husband, a betrayed wife, a wealthy person, a poor person, an angry person, a person who has conquered and moved beyond his anger. Sometimes this works, and sometimes it doesn't. The dynamics in the marriage between Virginia and Tim are never satisfactorily developed. The script tries to give Virginia a partially redemptive passage, but Tim's fleeting moments and blank reactions leave him unknowable. Estevez does little better with Jack and Samantha, and the estimable Helen Hunt, in particular, is provided very little to work with. But elsewhere the characters develop both depth and grip. John's story is revealed with great subtlety, and Jose's generates unexpected power. And people like me will be stirred for all of them as the senator falls, a genuine light of hope snuffed out for a generation.