I Was a Teenage Talent Chauffeur
My two summers spent driving celebrities to Wolf Trap.

One hot August afternoon, I struggled to keep my cool as I steered a passenger van through DC construction. We rocked violently over the potholes as Elvis Costello, seated behind me, swore loudly with every bump and jolt.
The summers after my freshman and sophomore years of college, I was a driver at Wolf Trap, an outdoor music venue in Northern Virginia. I’d interned at Wolf Trap my senior year of high school and could hardly believe it when I heard that they hired college students to drive the talent.
Hey, I thought, I was about to be a college student. I could pick up Trisha Yearwood from the airport!
Training was minimal. My first day, I was handed a beeper (mind you, this was 2002) and sent out with a veteran driver whose only advice was:
- Avoid Earth, Wind, and Fire (only guys drove those shifts).
- If lost, act like I knew where I was going.
We spent our days backstage reading trashy paperbacks and challenging each other to Mario Kart. These lazy stretches were interrupted by airport runs or errands like searching several Dollar Stores for the same purple plates that Jewel had dined on in Vegas. Veterans regaled us newbies with factoids like how Aretha Franklin required half of her payment in cash up front and carried it on stage, or how the alleged size of Huey Lewis’s manhood had created such a rabid fanbase that extra staff was needed to keep them at bay.
This was in the back of my mind when I drove Huey and the News to the airport after the show. He sat up front with me, talking about his son’s baseball team and asking me about school. Pulling up, we startled an older man and woman removing their luggage from the car directly in front of us. Huey hopped out and walked right over to them. What a nice guy, I thought, only realizing later that the man and woman were Bob and Elizabeth Dole.
I relished the job’s combination of the mundane and surreal. Depending on the day, my only interaction might be with Willie Nelson’s guitar tech as he showed me the collection of bras thrown at Willie on stage, hung from the trailer and swaying in the breeze.
Nothing is more enticing to a certain type of musician than a barely legal girl. My interactions with everyone were solidly PG, but my age was definitely a focal point for some passengers. I could have made a lot of bad decisions at the end of a night shift, but I was in a long distance relationship the first summer and in a bit of a depression the next. Finishing the latest Harry Potter (Order of the Phoenix, so Harry’s mood mirrored mine) and replicating recipes from the Food Network was more appealing than hanging out with Meatloaf’s roadies.
Overall, everyone was incredibly warm and generous, or at least polite. There was no diva behavior to speak of—although word spread quickly not to look directly at Beck or Ani DiFranco.
There were a few hair-raising moments, the kind you’d expect with teenagers behind the wheel.
When picking up Keith Lockhart, conductor of the Boston Pops, I was busted for driving on an expired license when security checked my ID. I was able to talk my way out of getting fired and promptly renewed my license, but it is still one of my most embarrassingly irresponsible moments.
While driving Peter and Mary of Peter, Paul and Mary, I almost sent Mary through the windshield when I slammed on the brakes to avoid a swerving car. Noting my grief-stricken face, Mary said, “Don’t worry, honey. We know it was his fault.”
I once cut a hard U-turn across four lanes of traffic with Big Head Todd and the Monsters in the back. Their flight landed several hours late, and someone had spotted the only fast food place still open at 2 a.m. in suburban Virginia. Gear went flying as the band yelled out their approval. Much like the time I sped off with Judy Collins, fresh off her set and concerned about fans in pursuit, I surprised everyone with my lead foot.
My most nerve-wracking experience happened during a routine trip to pick up lighting gels when I accidentally cut off another driver on the highway. The driver honked and tailed me for several miles, following as I drove down side streets and, eventually, blocking me in a busy parking lot. I’m not sure why they didn’t get out of the car. Maybe they could see that they were gunning for a frightened girl barely out of high school. I still think about what might have happened if they hadn’t driven away.
There were also moments of extraordinary beauty. Tony Bennett, who looked old and frail in the Cadillac’s backseat, came to life on stage. In his element, he looked and sounded like a man decades younger. Wynton Marsalis toured with a group of boys as part of his mentoring program, and at least one of those boys was always with him when he went for soundcheck or promotional appearances. He improvised a song based on my name as we coasted down the highway.
I always enjoyed sitting outside and listening to the strains of the National Symphony Orchestra soundcheck floating through the trees. But my favorite part of the job was the one-on-one conversations I had with various techs, musicians, and theater company members. There was so much downtime to fill without smartphones to distract us. I wonder how many of those conversations happen now.
I didn’t return the summer after my junior year. I had my own celebrity anecdotes and the nerves of steel that come from driving through city traffic. It felt like time to move on.
Over a decade later, I still look up Wolf Trap’s summer lineup and imagine driving certain artists to and from the venue. (Sufjan Stevens and Bob Dylan? Come on!) I may be a wife and full-time working mom, but part of me will always be that slightly irresponsible girl, acting like I know where I’m going.
This article is part of our ‘Summer Series’ collection. Read more stories here.
Jenna Gadient forgot her Twitter password long, long ago. She thinks it is all for the best.
Support The Billfold
The Billfold continues to exist thanks to support from our readers. Help us continue to do our work by making a monthly pledge on Patreon or a one-time-only contribution through PayPal.
Comments