There are some artists who have such a great repertoire of songs that it’s impossible to pick their absolute best. If you had to pick just one song of some of the greats that we grew up, like say Madonna, could you? Evidently, City Winery couldn’t when it held its Madonna wine pairing of 30 songs, 30 wines.

In anticipation of the event people speculated what wines would be paired up with “Like a Virgin,” “Like a Prayer,” and “Justify My Love.” I suspected “Like a Virgin” would be a young never before touched beaujolais nouveau (even though it’s out of season), “Like a Prayer,” a Bordeaux from Saint Emillon, and “Justify My Love,” perhaps a White Zinfandel because it’s a wine people need to justify their love for. The only notable “wine”of the three songs, was the non-alcoholic “City Winery Kid’s Sauvignon Blanc” that City Winery chose for “Like a Virgin,” to which I have two comments a) why bother giving us a fake wine and b) are they actively encouraging kids to drink wine? That better appear as apple juice on the menu when bambinos are allowed in!

The event started when we heard a man off stage singing the lyrics to “Holiday.” We thought we might be treated to a female impersonator, but no such luck (although later we did see a famous drag Queen who has appeared on Project Runway named Acid Betty). However, our MC did not disappoint. He even came armed with a Geisha like fan which he used to fan himself. That man had some serious sexy Geisha fan moves. Note to self, buy a Geisha fan.

BTW, I have solidified myself as a hag as it was easier for me to get more numbers from gay men than it is for a dog to pick up fleas. I was honored when I was invited to come with them on their next adventure, but since it was straight love I was looking for, I politely declined.

I took notes during the different flights. I can read the earlier ones and I will admit on the second half of the sheet, I am unable to decipher the babble. The legible notes next to the corresponding number of wines are as follows:

3. La Isla Bonita = Sauvingon Blanc: “Are they seriously serving a white wine with a passionate song like this? I picture a fiery passionate red.”

4. Material Girl = Rose: “We are starting to do the camp fire sing along at this point and the line ‘Boys may come and boys may go and that’s all right you see’ was sung at a particularly high volume in unison.”

8. Papa Don’t Preach = a white wine I’ve never heard of, but I evidently liked because I starred it on the wine list: We are starting to sing while we toast at this point. We debated whether this was the video where Madonna wore the “Italians do it better” t-shirt. It was. I remembered it because when I was like 8 and I watched it on Friday Night Videos (we didn’t have cable), I thought it was a cool shirt. I wasn’t sure what “it” was, but it made me want to be Italian. I also laughed as I now recognized that she and her “baby” were riding the Staten Island Ferry on a date. Obviously Madge was slumming it in her pre-living in a material world days.

10. Rain = Muscadet: Our MC dramatically announced that rain was a metaphor for tears. I thought he was going to go deeper with this analysis to introduce the Muscadet, but he didn’t. Bummer.

12. Ray of Light = some random white wine: Me to a friend, “This tastes dry, does it taste dry to you?” My friend, “I think it’s as fruity as this whole room.” Clearly, my palate is having an off day.

A discussion ensues over why City Winery was only able to obtain 18 of the 30 videos (IP issues or availability-my friends in the music industry swear it’s b/c of IP issues, I take their word for it). So instead of 30 videos there is a “Moments of Madgeness” compilation of videos for the other 12 songs.

16. Borderline = we have now switched to red wine: “I wrote fashion glasses?” At first I have no idea what this means, but now I remember we were trying to figure out if our hipster and pseudo-pushy waiter’s glasses were fashion glasses or real glasses. Consensus, fashion glasses.

18. Express Yourself = Barbaresco: At this point we’re in FULL girl power mode as we all belted out as our toast, “DON’T GO FOR SECOND BEST BABY.” The rest of my note on this point is indecipherable.

22. Justify My Love = some red italian wine: MC sings “I want to kiss you in Paris, I want to hold your hand in Rome” and then he says “this wine makes me think of an Italian boy…it tastes like an Italian boy, it smells like an Italian boy and who doesn’t love Italian boys.” I must LOVE Italian boys as I starred this one.

23. Don’t Cry for Me Argentina = Malbec, obvi: Dear God, I’m not sure if it was my love for Argentina or Malbec or what, but I am now signing full blast “DON’T CRY FOR ME ARGENTINA, THE TRUTH IS I NEVER LEFT YOU, ALL THOUGH MY WILD DAYS, MY MAD EXISTENCE, I KEPT MY PROMISE,” while raising my glass to the MC who is acting very Evitaesque while Geisha fanning himself and looking at me and loving the Evita like adoration.

26. Beautiful Strangers = another new red wine: Disclaimer as my scratch paper has been highjacked because I’m on the dance floor at this point. The note says, “Madison is dancing with beautiful gay strangers.”

The rest of the night involved me getting called up to stage because it was my birthday at which point the MC spanked me with the microphone. Weird, but first official birthday spank. Next year, I’m asking for the Geisha fan.