Regattabar Jazz Club

The Regattabar Jazz Club is a live-music venue in Harvard Square, Cambridge, Massachusetts, remembered as the setting for a striking encounter between expectation and chance. During a solo visit to hear pianist Tommy Flanagan, the narrator silently settles on two unlikely requests; Flanagan then plays both, turning an initially disappointing set into an unforgettable one.

Setting and Reputation

From 1993 to 1995, the narrator lived in Cambridge, Massachusetts, where he was a writer-in-residence at a college and worked on The Wind-Up Bird Chronicle. The Regattabar Jazz Club, in Harvard Square, offered frequent live performances in a comfortable, relaxed, cozy atmosphere. Famous jazz musicians appeared there, and its cover charge was reasonable, making it a welcoming place to hear performers of distinction.

Tommy Flanagan’s Performance

One evening, the narrator went alone because his wife had other plans. A favorite pianist, Tommy Flanagan usually performed as an accompanist; the narrator admired the warmth, depth, and steadiness of his playing, as well as his solos. Seated near the stage with a glass of California Merlot, he anticipated a memorable night. The performance, however, initially seemed to lack the special quality that could carry a listener into another world. As the set continued without improving, the narrator began to fear that it would end as a disappointment—and that he might never again see Flanagan perform live. In fact, he never did.

The Unspoken Requests

While listening, the narrator imagined what he would ask Flanagan to play if given the chance to name two songs. After considering the possibilities, he chose “Barbados” and “Star-Crossed Lovers.” These were not obvious requests: the first was a less showy Charlie Parker piece, and the second was a Duke Ellington tune that the narrator believed many listeners had never heard. His choices came from Flanagan’s recorded solos on both pieces, whose crispness and intelligence had stayed with him. He knew the imagined exchange was exceedingly unlikely; he had not voiced the requests or even spoken with the pianist.

Coincidence and Significance

Without addressing the narrator or looking in his direction, Flanagan began the set’s final two numbers with “Star-Crossed Lovers,” then followed it with an up-tempo “Barbados.” The narrator sat speechless, astonished by the astronomical odds that Flanagan would choose those exact songs from the immense range of jazz repertoire. More than the coincidence itself, the performances mattered: both were extraordinary, supplying the magical glow the evening had seemed to lack. The club’s remembered significance rests on this reversal—from private disappointment and an unspoken wish to a pair of performances that became the narrator’s lasting memory of hearing Flanagan live.