Reality TV show: The Real World: Boston (1997)

Remember him? The all-American lumberjack from the Boston house that used to spar all the time with Kameelah and wastedly converse with Montana about apes masturbating for oranges? He could've opted to forgo real employment in favor of never-ending Real World/Road Rules challenges like other show alums (he did 2002's Real World/Road Rules Challenge: Battle of the Seasons), but he decided to take the road less traveled. After serving as a district attorney in his native Wisconsin, he's now quite literally running shit (or helping) as a Republican U.S. Representative for the state's 7th congressional district.