Georgetown, Dizzy Gillespie, and You

By Phil Perkins | January 7th, 2025

Remembering a cold and romantic evening in D.C.


Dizzy Gillespie, seen in this remembrance in Georgetown, D.Cl

As years go by, memories pile up like leaves on a breezy autumn day. Boomer reader Phil Perkins recalls a trip to Georgetown in D.C. and a chance to see Dizzy Gillespie.


Now here’s a romantic Boomer story for you. You were in the mood for one, weren’t you? I thought so. It happened when my wife Sandi and I were in our 30s or maybe 40s. Doesn’t matter. When did Dizzy die? I’ll look it up or you can.

We were in Georgetown for a little downtime. It was the holiday season, and we always enjoyed spending time shopping and dining in that magical area of the nation’s capital at that time of year. Walking along M Street had become a regular treat for us during our annual trip to Northern Virginia and the District. We had staked out our regular evening haunts and breakfast choices. Moreover, our preferred bed-down selection was the Georgetown Inn, where we had even become familiar with the service people and learned to tolerate the weird parking challenges. The good news was that the quiet bar there offered a nice late evening stop for high-end Cognac and coffee.

But I digress.

We had elected to have dinner this one evening across the street from our hotel at a well-known pasta joint where the clientele were shoulder to shoulder, up-and-comers talking deals both business and governmental. It was stimulating if a little intimidating. Most of the shoulders we bumped into were attached to well-heeled 20-somethings in very expensive suits still clutching briefcases as they slurped the latest trendy cocktail. After finally jockeying our way to a table and eating our fill of pasta, we headed to Blues Alley on the chance that we could get in to see Dizzy Gillespie. Now we knew it was a longshot. He had been advertised for some time. But we were familiar with the club, having been there several times, and knew there were often “no shows” allowing for folks like us to show up late and beg a table.

For those not familiar, Blues Alley is as advertised – a small club down an alley. It had hosted some of the most storied blues and jazz artists of our time. We had even seen Nancy Wilson there. No not Ann’s sister … the earlier jazz version. The one who was also an actress. Come on boomers, you remember her.

The club is intimate, dark and romantic.

We let the people at the door know we were waiting for any cancellations and decided to stand outside and just be patient. It was quite chilly that evening, of course, and unfortunately, it began to rain. We figured the temperature must have teetered on the freezing mark and sure enough after some amount of time the rain turned to snow. I have to admit that we debated how determined we were to see Dizzy as our resolve began to erode. But we decided to stick it out at least for a while longer.

Okay, here’s the romantic part. We ended up standing outside the club with our arms wrapped around each other, head on each other’s shoulders from time to time for what must have been another half an hour as the rain turned to snow and the snow to rain.

Other people who had arrived earlier and were waiting for cancellations were called in one by one as our hopes sank, along with our body temperatures. After a while, it was just us, alone in an alley, wet, cold and dispirited … cuddling to stay warm. Just as our patience was at its end, the door opened.

“We have one more table,” the man said, smiling broadly.

We couldn’t believe it. Whether we saw Dizzy or not, the warmth would be a welcome change. Actually, we assumed that the “table” he mentioned would end up being a spot at the bar. But we had no idea what awaited us. We were surprised to be shown to a table right up in front of the stage. When Dizzy was introduced, he was directly above us. Spitting distance, if you know what I mean and if you know anything about Dizzy Gillespie.

But we couldn’t have cared less. Our patience paid off. We were in the cozy blues and jazz club that we had loved for years, down an alley, seeing one of the greats.

True story. One of many. Life is good my friend, life is good.


FEATURE IMAGE, TOP, CAPTION: JPRoche, CC BY-SA 4.0, via Wikimedia Commons. 


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