It was the best of Bond, it was the worst of Bond
The cinema of James Bond often gets broken down by his accessories—the cars, the guns, the gadgets, the songs—but after all the martinis have been shaken, not stirred, the quality of a Bond film is directly related to the quality of the Bond. Six actors have played the iconic British superspy over the course of 23 “official” Bond films (the upcoming Spectre makes 24), and each one left their mark on the role, for better or worse.
Best Bond: Sean Connery
The all-time no-brainer. Daniel Craig has undeniably reinvigorated the franchise, but you could cast Hologram Tupac as James Bond and the role would still be associated with Connery. His charisma packaged with a titillating formula created a new genre, and beyond any feelings of nostalgia and birthright, Connery's films are consistently good, with Goldfinger remaining the franchise gold standard.
Worst Bond: Pierce Brosnan
You thought I was going Dalton! Sure, Timothy Dalton was a lousy Bond, the star of two unmemorable films, the better of which prominently featured Wayne Newton. But at least he was a Bond for his times, leaner and meaner to match the action heroes of his era. Brosnan's Bond was four interchangeable movies of money-grabbing sleepwalk, producing most of the worst Bond films.
Second Worst Bond: Timothy Dalton
Because, seriously. Dalton's brooding outlaw Bond is probably the closest precursor to Craig, but he never fit the part, and his movies are cut-rate.
Incomplete Bond: George Lazenby
Lazenby only made one Bond movie, 1969's On Her Majesty's Secret Service, and then declined to return for the follow-up. On Her Majesty's is often (ignorantly) cited as a failure, but it's a solid entry, taking the character in a slightly more realistic direction after the ridiculous You Only Live Twice.
Unofficial Bond: Sean Connery (and others)
The Albert Broccoli family has owned the movie rights to James Bond since 1961, but a few “unofficial” Bond movies have been made outside the Eon Productions canon. Before the Craig version, Casino Royale was first made into a 1950's TV episode with Barry Nelson, and later into a semisatirical monstrosity starring David Niven. Connery also made an unofficial return in 1983's non-Eon Never Say Never Again, a remake of his 1965 success Thunderball.
Problematic Bond: Roger Moore
The Bond movies are extended male fantasies, and there's no more outlandish male fantasy than a lumbering, leering, bronzed and creased Moore playing an action hero who magnetizes women to his dick.
Bourne-Again Bond: Daniel Craig
After decades of smirking sex-predator Bonds, the role was rebooted for Daniel Craig as a dark, intense badass, a change that put the character in line with contemporaries like Jason Bourne (not to mention modern sexual harassment policies). Craig brought Connery charm and modern physicality to Dalton's seething outsider figure, but the changes made the character seem less like James Bond and more like everyone else. Still, 2013's Skyfall left the franchise well-tended yet open-ended, and that uncertain future makes the upcoming Spectre all the more enticing.