Before making a huge impact in Smokey and the Bandit (1977), Reynolds had spent many years kicking around in TV shows, mostly playing villains and his career was going nowhere. Tarantino based his film on his experience growing up in Los Angeles in the sixties and seventies. Reynolds did not leap from obscurity until Tarantino was 14 years old. It is interesting that Dalton supposedly played the bad guy role in the featured episode of The F.B.I. (1965) - a role that was played in real life by Burt Reynolds.
When Rick is talking with Trudy he says that in fifteen years she would be washed up as well as him. Kurt Russell was one of an extremely small number of child stars who continued to have a strong career through adulthood. In fact, he was the only one to end up with high-profile roles into his senior years, having made this particular film at the age of 68.
The opening scenes show two good guys responding to a late-night horse theft and riding off without cowboy hats, making the audience wonder if this was present-day. Presumably Wanamaker rationalized this hatless aspect as depicting haste, yet he forgot about how this might be interpreted by an audience. Also, they were both wearing plaid shirts, with was also odd. Plus much of the camera work, angles, sudden zooms and the like were very strongly influenced by TV detective shows of the day. These were reflections of Wanamaker's personality, which no doubt were noted by Quentin Tarantino when scripting and directing the Wanamaker portrayal.
It might also be noted that Leonardo DiCaprio's scruffy, shaggy-haired, mustachioed hippie-villain in this film was very closely modeled on the look that Wanamaker designed for the original actor, Joe Don Baker.