Our previous Prime Minister, Conservative Steven Harper, ruled as a kind of tyrant for ten years. He really did not play well with others.
Before him was Liberal Paul Martin, who was in office for three years, and beset by attacks from Conservative opponents for a lot of that time. I don’t remember anything about his relationship with W. He certainly met with him, though not at the White House. Martin was rather forgettable as a PM, to be honest.
Before that was Liberal Jean Chrétien (not Jean Poutine), and he did visit the White House while Clinton was in office. But Chrétien was not particularly friendly to Bush, for obvious reasons. Bush had expectations of Canadian support in his war with Iraq, and he was disappointed. My guess is that this may have created some lasting distance between our countries.
More generally, for the most part over this twenty year period, we have had conservative leadership while you have had liberal leadership, and vice versa – so things have not been as friendly as they could have been. The last visit was when Clinton and Chrétien were both in power – and both are liberals (at least, Clinton is considered relatively liberal from the US’s point of view). Chrétien was a charismatic leader who spoke his mind freely – reminiscent in some ways of Pierre Elliott Trudeau, Justin’s father.
Trudeau and Obama are fairly well-matched in terms of personality and ideology. It will be interesting to see how the next US leader interacts with our PM.