Since 1995, the Recording Academy has compiled annual CD sampler releases spotlighting major Grammy Award nominees in the weeks before the show. These are usually carefully curated and have proven strong sellers, and this year’s edition entered the album charts at No. 4 last week. But the selection of songs illustrates some problems behind the awards themselves.

Of 22 songs on the “2011 Grammy Nominees” album, a full 10 were actually released prior to 2011.

Of course, the Grammy Awards eligibility period does not conform to the calendar year – extending from September 2010 to September 2011 – and that explains Nicki Minaj’s “Super Bass” and Taylor Swift’s “Mean” (both on albums released in fall 2010). But then there’s Katy Perry’s “Firework,” released on “Teenage Dream” in August 2010, and Mumford & Sons’ “The Cave,” released in the U.S. in February 2010 and available in the U.K. since fall 2009.

Most notably, three songs on the “Nominees” compilation up for this year’s record of the year statuette were actually performed on last year’s Grammy kudocast, “The Cave” among them. When Mumford performed the song at the Grammycast, it was already a year old. If it wins record or song of the year this weekend, it will have turned two.

The reasons this sort of Grammy lag is possible lie not only in the early-closing eligibility period, but also in the language used to describe the awards.

For example, a song from a previous year’s album can be eligible for record of the year in the next, provided that album did not win a Grammy and the song was not entered as a record of the year contender in the previous year (for this reason, Perry’s “Firework” is eligible).

Song of the year, on the other hand, is awarded to a song “first achieving prominence during the eligibility year.” So acts that experience a slow build in popularity – like Mumford, for example – aren’t hemmed in by overly rigid deadlines. But this “achieving prominence” designation can be vague, with echoes of the long-contentious best new artist category, whose slippery criteria allows both Nicki Minaj (Grammy nommed last year) and Bon Iver (whose debut album landed on critics’ top 10 lists in 2008) to contend for best new artist this year.

It’s not a new problem – Paul Simon’s masterpiece “Graceland” won album of the year in 1987, with the song of the same name winning record of the year in 1988 (after losing song of the year in the previous year). But as cultural tastes continue to move at an ever accelerated pace, with individual songs available for purchase as de facto digital singles long before they’re officially released as such (and thereby “achieve prominence”), this makes less and less sense. By hewing to distinctions that are either highly subjective or else increasingly tangential, Grammy does itself no favors, slowing down when the rest of the music world is speeding up.

Of course, nitpicking the Grammys is a long and somewhat tired pursuit, and the Recording Academy has made strides to contemporize. Fortune also shines on this year’s ceremony in the form of Adele, going for record, song and album of the year with her “21” still atop the album chart.

But more can be done to ensure the awards are both timely and sensible. The last three months of 2010 saw the releases of Swift’s “Speak Now,” Kanye West’s “My Beautiful Dark Twisted Fantasy” and Minaj’s “Pink Friday” – all ineligible for last year’s Grammys, together representing 10 noms for 2011. That these blockbusters dropped so late in the year was hardly a coincidence; they were released for the holiday shopping period, much as Grammy-friendly yet ineligible albums by Florence and the Machine, Drake and the Black Keys were in 2011.

The Grammys will never be perfect, but allowing the most high-profile releases in a given year to be eligible for that year’s awards, as well as stopping the spread of a single album’s material into multiple years, would be a good start.