I tossed beads off the balcony and she caught them. My night out on Bourbon Street New Orleans, 2008 was about to change. She called herself Brit, blending in the crowd of drunk revellers, surrounded by her entourage. I was couch-surfing - sharing one sofa in a living room with 3 New Zealanders, she was cute and I was tipsy, so it didn’t take much convincing when I was soon whisked away in a van. It wasn’t until we were driven back to a hotel when one of her friends howled “he doesn’t know your last name does he!?” I was none the wiser.
“Evening Miss Spears” said the doorman as we stumbled in.
It sunk in. I couldn’t believe it at first, but also couldn’t wait to tell my friends who I’d spent my night with. Nobody would believe me.
I must have left an impression as I was put on her guest list, free flights anywhere within the USA. I visited her hometown and her family between her busy schedule, each time we met I laughed to myself “Oops, I did it again!” After a blurry few weeks it was all over.
A month later I was performing in Scotland in a basement bar, when one night in the back of the room she appeared unannounced, just showed up to surprise me. She stayed a few nights on my mattress on the floor of the room I was sharing with another comedian then returned to America. This was far from Rock’n’Roll or like any hotel room she was used to!
A month later I attended a friend’s bachelor party at Oktoberfest in Germany, his wedding was in NYC but I couldn’t afford to attend both, until she reminded me of the perks. And so, I flew from Munich to NYC (only having to pay the taxes) for 33euros ($50USD). Every airport, immigration would interrogate me, “and who are you sleeping with to get such cheap flights!?” They never believed me, but upon checking her name in the system would do a double take and their jaws would drop.
Of course, being back in the US, we reunited and met in a small town in Ohio, where she told me, my comedy idol, Dave Chappelle lived. It was a tiny place and sure enough, we walked by him on the street. I was star-struck. I simply HAD to meet him! I followed him until he was sat alone on park bench smoking a joint. I got the confidence to start chatting. Assuming I was just another fan at first, he hesitated but relaxed when he realised I was a working comedian, he’d also performed the Edinburgh Fringe early on in his career and we shared some stories, shook hands and he wished me well. I asked for a photo but he declined, hinting at his distrust of the media and paparazzi following his well-publicised recent departure from the limelight. He also looked very stoned so it might not have been his best photo. Fully understandable that he wanted to lay low, I was once again left thinking that none of my friends will believe who I’ve just met. Brit and I laughed as we both knew the ridiculousness of the situation, and she said what we were both thinking,
“well, you can always tell them you were with me!”
I took advantage of one last flight perk, first class from Philadelphia to Manchester, UK for a mere $100 total.
Perhaps I should clarify, Brittany Spears was an airline stewardess. She has since married a pilot and I no longer get the perks. We’re still friends.
Dave Chappelle was and still is THE Dave Chappelle.
He was lovely. We’re not friends, yet.
I’ve never met Britney Spears the pop star, but I’m pretty sure she’d fly halfway around the world to see me.
Happy Travels xo