No, it's not remarkable that Ryan keeps getting reelected by wide margins
I don't usually nitpick weak media coverage of electoral politics, but I take it personally when it's about the place where I grew up. Yesterday Renee Montagne interviewed Brad Lichtenstein, who recently shot a documentary about Janesville, WI. The film isn't specifically about congressman and vice presidential candidate Paul Ryan, but lucky for Lichtenstein, the city's most famous son is all over the news this week. Toward the end, Montagne marvels that "Paul Ryan, a Republican, has remained to this day popular in a traditionally Democratic-leaning district."
Lichtenstein's work, as he clarifies in response to Montagne, is focused on Janesville, not the rest of Wisconsin's first congressional district. But for what it's worth, the district overall is not traditionally blue; it's a longtime swing district that has recently leaned slightly right. Bush won a majority there in 2004; Obama did the same in 2008. In each case Wisconsin 1 went a couple points redder than the nation generally.
As for Ryan's seat itself, it's true that Democrat Les Aspin held it for more than 20 years (till President Clinton appointed him to run the Pentagon). Republican Mark Neumann, who this week lost the Republican primary for U.S. Senate, picked the seat up in the 1994 takeover—as part of a massive, nationwide sea change in congressional power. Ryan took over for his fellow Republian in 1999 and has held the seat ever since.