Perhaps the biggest obstacle to demolishing the filibuster is the cynicism and defeatism of those who assume this can't be done. The obstacles are fearsome, but they cannot be worse than the obstacles faced by the generations of activists who called for, and eventually won, direct citizen election of US Senators via the 17th Amendment to the US Constitution, ratified April 1913. I mentioned this in comments to a recent diary on the filibuster by Chris, and there was some objection to the comparability of the fight for the 17th to the filibuster, so I wanted to elaborate on the magnitude of this victory to make clear that yes, bigger and more difficult Senate reforms have been done than ending the filibuster.
No mistake about it, the 17th Amendment was an epic battle, one that began as early as 1826 (when the first amendment attempt appears in Congress). After its passage, Wilson's Secretary of State, William Jennings Bryan described it superlatively as the greatest reform attained in over a century. It's hard to agree with that, given the importance of the 13th, 14th and 15th Amendments, but does make it clear that a major contemporary populist figure viewed this as a big victory.
Consider the situation prior to its passage: The amendment to require Senators to face election must get passed by two-thirds of the Senate, a chamber of men selected, not elected, by the legislatures of their home States (sometimes with only plurality support). After this, three-quarters of the State legislatures would then have to ratify a measure decreasing their power and influence over the more powerful chamber in the national government. All the built-in incentives were opposed to this.
Here's how the New York times described the issue, the day after the 17th Amendment passed Congress in 1912 (transcribed from PDF at link by me, errors mostly mine):
Via commenter "the new" in quick hits, we learn (surprise) that long time foe of democracy George Will opposes mandating special elections for senators. Will's column is amusing because he can't constrain his rage against the proponent of this Constitutional amendment, Senator Feingold (D-WI) for his past work on the McCain-Feingold campaign finance legislation. Let's take a look at what the brightest light of the conservative intellectual movement has to say this Sunday.
Sen. Feingold's Constitution By George F. Will
Sunday, February 22, 2009; Page
A simple apology would have sufficed. Instead, Sen. Russ Feingold has decided to follow his McCain-Feingold evisceration of the First Amendment with Feingold-McCain, more vandalism against the Constitution.
You'd think a guy who was just proven a liar over his column denying global warming would be shy about demanding that other people apologize for things, but that's the utterly shameless true conservative, George F. Will for you.