When character are introduced, it’s usually very easy to see whether or not they will be an ally to the main character, or an antagonist---writers try to establish a character’s stance within the first five minutes of the first scene featuring them. Nine times out of ten, that’s what the writers go for, and the ratio seems to be about the same for the many characters that Simon Oakland has played; the opening scene of the “Justice Deferred” episode of Bonanza, for example, shows you everything you need to know about Mel Barnes---the twist being that it takes a while for the other characters and the audience to realize that it was Mel Barnes and not his unfortunate lookalike Frank Scott.
However, sometimes, it is that remaining one character out of ten that is the most intriguing---the antagonist with the hidden depths, the antagonist with the surprisingly sympathetic backstory, or the antagonist who seems like an adversary while really being on the same side as the protagonist and respecting them. Given Simon’s preferred acting method of trying to make all of his characters as multifaceted as possible, it is in roles like these that he shines even more brightly than usual.
Jim Nation from the “Overland Express” episode of Gunsmoke is a prime example. His first scene features him shooting at Matt and Chester, clearly on the run from them, and, upon his surrender, Matt confirms that Nation is wanted for murder after killing a man in Dodge City---to which Nation insists that it was in self-defense. At this point, neither Matt nor the audience knows whether or not to believe him, and they are left wondering again when, as they ride the stagecoach back, Nation insists that one of their fellow passengers is a wanted murder who is likely planning to hold up the stagecoach. When this turns out to be true and the man demands that everyone surrenders, Matt counters Nation’s “I told you so” with a request for help---for Nation to pretend that he’s going to side with the murderer so that he can make his escape and avoid being put on trial for the murder he committed. Even Nation is surprised by how much trust Matt is giving him. Luckily for Matt and everyone, Nation is absolutely sincere and plays his part marvelously---the same man who, in the episode’s beginning had been shooting at the protagonist, ended up being the hero. And even when Nation realizes that he has the chance to truly escape, he decides not to take it and willingly returns to Dodge with Matt to stand trial---after which Matt promises him that that Nation’s character is enough to convince him to testify on his behalf that he would only kill a man in self-defense.
Another example would be Simon’s portrayal of Sgt. Driscoll in the “No Sanctuary” episode of Medical Center. Driscoll appears to be using rather callous methods to try to get an assault victim to identify her attacker, ignoring the doctor’s insistence that she is in no condition to talk about it, still in shock and trying to recover from a punctured lung. Furthermore, he brings the suspect to the victim in the hopes that she will confirm that she knows him, yet only succeeds in nearly giving her a complete breakdown. Without a positive identification, however, Driscoll has to let the suspect go, yet continues to tail him, only to be shot by the suspect once he figures it out. Facing an operation performed by the same doctor he had been clashing with earlier, Driscoll eventually reveals to him that his late wife was killed during a similar assault incident---and that he had to let the perpetrator go because no one would identify him, explaining his furious zeal in pursuing this particular case he had been working on, giving a heart-wrenching and sympathetic side to an otherwise abrasive character.
Even Tony Vincenzo, one of Simon’s most famous roles, started out like this. In the first Night Stalker movie, most of his scenes seem to suggest that his character is there to stand in Carl Kolchak’s way as he tries to save Las Vegas from a vampire. It’s only in the final scene that Carl and Tony share that it becomes apparent that Tony really does respect Carl---something that becomes clearer in the second movie and then the series proper as Tony evolved from adversarial boss to concerned boss. Tony still doesn’t believe in the monster stories that Carl uncovers and still refuses to publish the stories, but his genuine concern for his unlucky employee manifests itself in more obvious ways, such as the numerous times Tony bails Carl out of jail or checking up on him if he hears him yell out in fear. It eventually becomes clear that, rather than being a foe, Tony is one of the very few true friends that Carl has.
Characterization has always been one of Simon’s strong points as an actor. And while it’s always fun to watch him play a straight-forward good guy, antagonist, or all-out villain, the true peak of his talents can be seen in the characters that keep you guessing---the books you can’t judge by their covers.