I have a love/hate relationship with the Grammy Awards. I love lists, and I love award shows, so even a minor-league award show piques my interest-and there’s nothing minor-league about the Grammys. This ceremony is to music what the Academy Awards are to movies. Not only is the receiving of this award a validation of sorts for the artists that win (after all, this award is voted on by other musicians as well as assorted execs and other industry folk), but it also pays dividends at the cash register-ask artists like Bonnie Raitt and Ricky Martin. Raitt’s surprise sweep in 1990 finally turned her into a superstar after decades of performing. Martin’s performance of “The Cup of Life” 11 years ago introduced him to a huge Middle American audience who had no idea who he was.

On the other side of the coin is the fact that the people who are part of the National Academy of Recording Arts and Sciences (the team that nominates artists and chooses who wins) have made some foolish choices over the years. An overly conservative block of voters has conspired to overlook some incredibly influential artists and bands over the years. Led Zeppelin never won a Grammy. Neither did Bob Marley. Other artists who have never won a Grammy Award: Diana Ross, The Clash, Hall and Oates, The Talking Heads, Public Enemy…need I go on? Smokey Robinson and James Brown have one Grammy each. The Rolling Stones have two.

There have also been some pretty major errors in judgment over the years. Remember Christopher Cross’s Grammy sweep in 1981? How about Jethro Tull winning the first Grammy ever awarded in a heavy metal category? Steely Dan’s “Two Against Nature” beating “Kid A” and “The Marshall Mathers LP” for Album of the Year in 2001? What about Herbie Hancock beating Kanye West and Amy Winehouse in the same category just two years ago? The fact of the matter is that the majority of Grammy voters are over 50 (and thus, out of touch with what current musical tastes and genres are) and comprise whatever the music industry version of the Old Boys’ Network is, which leads rock crit-types (or really, anyone with more than a passing interest in contemporary music) to go batsh*t insane every year when the nominees and then the winners are announced.

This year’s nominees are not so much out of touch as they are predictable. For better or for worse, this year’s big nominees represent what was actually popular in 2009. So the leading nominees are R&B diva Beyonce Knowles, country sweetheart Taylor Swift, dance diva Lady GaGa and (it pains me to write this) The Black Eyed Peas. All of the above named artists are talen-three of the four above named artists are talented, but even in what was a pretty crappy year for music, it’s hard to argue for any of these folks being the best that the industry had to offer last year.

At any rate, I’ll be bringing you my predictions in the major categories and genres (except for country, which I will admit is not my most knowledgeable genre, despite more than a passing interest), with all the appropriate commentary. My success rate over the years has actually been pretty good, which should clue you in on how predictable the Grammys really are. Or maybe I have the inside track and actually know who the winners are before they’re announced? (No, that’s not the case. Although several people I know receive ballots, they’re quite tight-lipped about their choices).

Anyway, we’re gonna start this party off with the rap categories. While the very first rap Grammy (back in 1989) went to the mom-friendly DJ Jazzy Jeff & the Fresh Prince despite the fact that the previous year was a watershed moment in hip-hop, the voters have gotten better about nominating and awarding quality with the passage of time. The past decade’s big winners have been Kanye West (who has won 11 of his 12 Grammys in rap categories) and Eminem (who has 9 of his own), and they’re the big nominees this year, although all of West’s nominations save one come from appearances on other artists’ records, and Eminem’s “Relapse” was of questionable quality, to say the least. Let’s take a look at the nominees, shall we? Anything to shut me up…

Best Rap Song (awarded to the songwriter)

Nominees: Best I Ever Had (5 songwriters, including Drake and Lil Wayne), Day ‘n Nite (2 songwriters, including Kid Cudi), Dead and Gone (3 songwriters, including T.I. and Justin Timberlake), D.O.A. (Death of Auto-Tune) (7 songwriters, including Jay-Z), Run This Town (5 songwriters, including Jay-Z, Rihanna and Kanye West)
Will Win: T.I. and Justin Timberlake
Should Win: Tough choice

Drake and Kid Cudi represent hip-hop’s new breed, and a win for either of them would represent a changing of the guard. Too bad that won’t be happening. Grammy has always been slow to recognize new talent, and the fact of the matter is that the older sector of voters recognize the names “Jay-Z” and “Kanye West” and not the names “Drake” and “Kid Cudi”. I’m tempted to say Jay-Z will win, but two things turn my vote in favor of T.I. One is the fact that Jigga is nominated twice and the two songs will likely split the vote, and the other is that the T.I. song has a socially redeeming message. Jay will win this award next year for “Empire State of Mind”, anyway. Hand this one to “Dead and Gone”, which, incidentally, is the best written song of the five and should win anyway.

Best Rap Album

Nominees: “Universal Mind Control” (Common),”Relapse” (Eminem), “R.O.O.T.S.” (Flo-Rida), “The Ecstatic” (Mos Def), “The Renaissance” (Q-Tip)

Will Win: Eminem
Should Win: Q-Tip

The nominees in this category should serve as a reminder of how much crappy hip-hop music has been made in the past year or so. This award is Eminem’s to lose (“Relapse” got some critical love, Eminem is a Grammy favorite, and the album sold more than the other four albums put together), but let’s take a closer look at the nominees for a second. Flo-Rida’s nomination is a f*cking joke, Common made a completely embarrassing album that was the worst of his career, and, quite frankly, “Relapse” didn’t do Em any favors, either. Mos Def and Q-Tip, despite making the only two albums here worth a damn, aren’t commercially successful enough to triumph. While Mos’s “Ecstatic” was a nice bounceback after the artistically shaky (I’m being kind) “Tru3 Magic”, “The Renaissance” is clearly the best album of the 5 nominees from a qualitative standpoint.

Oh, for those wondering where Jay and Kanye are: “808s and Heartbreak” was considered ineligible for the rap categories, and “The Blueprint 3” was released after the eligibility deadline and will most likely be nominated next year.

Best Rap Solo Performance

Nominees: “Best I Ever Had” (Drake), “Beautiful” (Eminem)”, “D.O.A. (Death of Auto-Tune)” (Jay-Z), “Day ‘n Nite” (Kid Cudi), “Casa Bey” (Mos Def)

Will Win: Jay-Z
Should Win: You get no argument from me here.

Here’s an interesting category with 5 relatively strong nominees. The same premise that held true for the Best Rap Song category holds true here regarding Drake and Cudi, despite the fact that “Best I Ever Had” and “Day ‘n Nite” were actually the two most popular songs here (Drake could potentially pull off an upset-this guy has a deafening industry buzz). Mighty Mos is uber-talented, but is out of his league  from a popularity standpoint. While Eminem has a chance, I think that at this point, Jay-Z has pulled in front of him in terms of Grammy recognizability, if only by virtue of his run as an actual record executive-people take care of their own. Besides, “D.O.A.” was the best of the five songs nominated here.

Best Rap Performance by a Duo or Group

Nominees: “Too Many Rappers” (Beastie Boys and Nas), “Crack a Bottle” (Eminem, Dr. Dre and 50 Cent), “Money Goes, Honey Stay” (Fabolous featuring Jay-Z), “Make Her Say” (Kid Cudi, Kanye West and Common), “Amazing” (Kanye West and Young Jeezy)

Will Win: “Crack a Bottle”
Should Win: “Make Her Say”

This is the most difficult of the categories to decide so far. If you put yourself in the head of the average Grammy voter, the only nominee you can definitely count out would be Fabolous-he doesn’t have enough name recognition, and the song he’s nominated for was an album track and not a single. The sympathy vote could go to the Beastie Boys, on account of MCA’s battle with cancer last year (and it would also give Nas his first ever Grammy), but seeing as a full recovery’s been made, I would bet against it (callous but true). The Grammy folks have been noticeably allergic to 50 Cent (who is Grammy-less so far in his career…and deservedly so, I might add), so even though “Crack a Bottle” was the biggest hit of the five nominees (hitting #1 on the Billboard singles chart), NARAS voters might pause when it comes to giving Curtis a trophy. Part of me still says the Aftermath trio will come out on top, but “Make Her Say” was just as big, has the intelligent/quirky/edgy factor going for it, samples one of the year’s biggest pop hits (“Poker Face”, which is nominated for Record and Song of the Year) and features previous Grammy winners Kanye and Common. Could go either way.

Best Rap/Sung Collaboration
Nominees: “Ego” (Beyonce featuring Kanye West), “Knock You Down” (Keri Hilson featuring Kanye West and Ne-Yo), “Run This Town” (Jay-Z featuring Rihanna and Kanye West), “I’m on a Boat” (The Lonely Island featuring T-Pain), “Dead and Gone” (T.I. featuring Justin Timberlake)

Will Win: “Run This Town”
Should Win: “I’m on a Boat”

Should “I’m on a Boat” even be in this category? Well, truth be told, Andy Samberg and his boy Akiva (is that a black name or what?) have better rhyme skills than half the rappers out there. I’d love to see this song come out on top for the pure comedy aspect. Hey, like Kevin Garnett, ANYTHING IS POSSIBLLLLLLLLLLLLLLLLE!!!!!

No, seriously. It won’t win. This award essentially comes down to two songs: “Dead and Gone” and “Run This Town”. While I gave “Dead and Gone” the edge in the songwriting category, I think “Run This Town” has the edge in the performance category. In this case, you have to consider the Rihanna factor. Her infamous assault at the hands of then-boyfriend Chris Brown took place before last year’s Grammy ceremony, and that fact alone could guilt a lot of voters into awarding a song that features her. The only roadblock? Kanye West, who is nominated in this category THREE times and could very well split the vote. In that case, T.I. wins, at which point Grammy will be saddled with a winner who can’t attend the ceremony (as T.I. is in a halfway house right now) and, if “Dead and Gone” wins in both the categories it’s nominated in, it will mean that of Justin Timberlake’s eight career Grammy wins, three of them will have been in the “rap” category. And that’s just weird.