Cyndi Lauper performs at the official afterparty. View the photo gallery >>

This past Sunday, I attended the 50th annual Grammy Awards in L.A., where it was a balmy 80 degrees—but who’s keeping track? This was my fourth time out (it’s a pleasure trip, and I pay my own way), and it never gets old. I’ll leave the debate over the Grammys’ relevance to other folks. I’m a sucker for awards shows—writers’ strike and all—but give me the Grammys over the Oscars any day; my concerts-to-movies ratio is around ten to one. Not to mention the fact that Chicago made an especially strong showing this year: Props to Kanye, Herbie Hancock, and Eighth Blackbird, among others. In honor of the Grammys’ golden anniversary, here’s a look back at close encounters of the celebrity kind from years past and present.

Grammys week is basically one big bash after another, thrown by magazines (People), record labels (Sony-BMG), and the artists the aforementioned attach their names to. Getting into the parties isn’t usually the problem; finding out about them is much more challenging.
Best of years past: Kanye West’s event in 2006, where I literally rubbed elbows with everyone from Jay-Z and Beyoncé (who turned an entire tent full of A-listers’ heads when they walked in) to Pamela Anderson, Nelly, Sacha Baron Cohen, Jeremy Piven, and Snoop Dogg. Kanye débuted his “Touch the Sky” video, starring Anderson, then hopped on DJ Mark Ronson’s mic to rap with help from John Legend and Common. Somehow I got smooshed in between the guys as they giddily traded verses. I had hoped to attend Kanye’s party this year (he led Grammy noms with eight and won four), but he didn’t have one—most likely, it was too soon after his mom’s untimely passing.
Best of 2008: Post-show I headed to the Staples Convention Center for the official afterparty, featuring performances by Natasha Bedingfield and Cyndi Lauper. I spotted a few familiar faces in the crowd, including Shar Jackson (K-Fed’s ex), who was standing next to me during Bedingfield’s bit. I was tempted to chat her up about Britney’s latest exploits, but she was busy with her young suitor. And hey, that would have been so un-Hollywood. Instead I gave her a knowing smile, made a dumb comment about how good Bedingfield’s abs looked in her midriff, and thrust my fist into the air in true rock ’n’ roll fashion.

And then there’s the music. But even before artists take the stage for the show’s televised performances, there’s a slew of rehearsals, concerts, and underground jam sessions. 
Best of years past: Back before John Legend was, ahem, a legend, I caught his pre-Grammys concert at L.A.’s House of Blues, where fellow guests included star couple Ellen DeGeneres and Portia de Rossi, and, who’s pretty much ubiquitous during Grammy week—and one of the nicest of the bunch. And then there’s The Roots’ annual bash at the Key Club; Dave Chappelle hosted it in 2006, when guests included Queen Latifah. In 2005, Tom Cruise was there, cheering on his friend Jada Pinkett Smith, who performed with Mos Def. I met the petite Mr. Cruise as he tried to sneak out the side exit (he was gracious and flashed me his signature grin).
Best of 2008: Nothing quite compares to catching Alicia Keys and John Mayer rehearsing the song “No One” at the Staples Center a couple of days before the big show. I was part of a small group of industry types who witnessed the practice session; we heard three run-throughs of the song—and not one sounded like a rough cut. Keys is one of the most amazing live performers I’ve seen—and she looked great, clad in jeans and a white V-neck sweater with a matching head wrap and sunglasses. During soundcheck she and Mayer hugged for about five minutes. From where I was sitting, it looked like they were old friends.

Finally, what everybody came for. Sure, the parties are great, but I’d happily trek to L.A. just for the ceremony.
Best (and worst) of years past: The first year I attended, in 2003, the Grammys took place at Madison Square Garden in New York, and I wore a floor-length gown and had my makeup done. That was also the year I met Diddy, whom I mistakenly called Puffy, and spotted Aretha Franklin and B.B. King hugging as they entered the auditorium. In the years since, I’ve learned that I’m practically invisible, so it doesn’t matter what I wear (this year, a silver sequined number that I bought off the rack hours before the event), as long as I’m in shoes that are comfortable for a long night of partying. Other lessons learned: Traffic is a nightmare. In 2006, I showed up so late I missed all of the red-carpet action and most of Madonna’s opening performance. I’ve also learned where to stand to spot celebs. In 2005, I got stuck in a pit of people funneling into the Staples Center, with a grimy Aaron Carter with dirty fingernails behind me.
Best of 2008: This year I timed my arrival just right, although the first celeb I saw was the bizarro actress Bai Ling, in what was probably the ugliest outfit of the evening. Grammy nominee and American Idol alum Chris Daughtry was also on his way in—he’s short; I’m surprised I even spotted him—as was Entertainment Tonight’s Mary Hart, who looked stunning in a beaded cocktail dress. But what I love even more than seeing the stars is the sight of everyone chowing down on McDonald’s inside the Staples Center before the show. It’s like these people haven’t seen food before (and by the looks of them, they haven’t).

I was tempted to join them, but I wanted to make sure I caught the opening act: Alicia Keys performing a “duet” with black-and-white footage of Frank Sinatra. The bit got a lukewarm response in the suite where I was sitting, along with the Houston Texans football players from that hilarious NFL Super Bowl commercial, Ephraim Salaam and Chester Pitts. The Ellen DeGeneres Show hired the guys as red-carpet correspondents for the Grammys, and they did such a good job she’s taking them on the road with her next month.

But back to the show and the free-flowing Champagne. It’s hard to rate the performances—I loved the Time with Rihanna, and Tina Turner shone next to Beyoncé (how does girlfriend dance in those heels at her age?)—but the most moving performance of the night was Kanye’s tribute to his mother, a heartfelt rendition of “Hey Mama.” It brought everyone in our suite to tears. And although most folks—including Kanye—seemed surprised that Herbie Hancock won Album of the Year (hey, as long as it’s a Chicagoan), and despite the show’s low TV ratings, I’d say it was the best Grammys ever. Then again, I say that every year.


Photograph: Sarah Preston