How Caribbean Wind By Bob Dylan Was Rewritten Multiple Times Before Being Abandoned

March 21, 2025

Bob Dylan, the legendary musician known for his poetic lyrics and powerful melodies, faced a challenging journey while writing “Caribbean Wind.” It was the early 1980s, a time when Dylan was trying to find new inspiration after a few years of creative ups and downs. He had just released a couple of albums that weren’t as well received, and he felt the weight of expectation pressing on his shoulders. Dylan believed that “Caribbean Wind” could be the song that would breathe fresh life into his career, but little did he know that this song would take him on a winding path of revision and frustration.

Dylan began crafting “Caribbean Wind” with vivid imagery and themes of longing and lost love. He was inspired by the beauty of the Caribbean, imagining breezy shores and vibrant sunsets. However, as he started recording and performing the song, he realized that the message wasn’t quite right. The lyrics felt clunky, and he wasn’t satisfied with the sound. Rather than giving up, Dylan tackled the song with determination, rewriting the lyrics multiple times. He would stay up late into the night, pouring over each line, trying to capture the perfect emotional tone. Each draft brought new ideas, but somehow, the essence he was searching for remained elusive.

As he worked on “Caribbean Wind,” Dylan would often experiment with different melodies and rhythms. One evening, while jamming with his band, he thought he had stumbled upon the key to the song. However, after a few performances, he felt the spark was fading. The audience responded with polite applause, but Dylan could tell his heart wasn’t fully in it. It was discouraging for him, as he had put so much passion into every word and note. He felt like he was chasing shadows, struggling to grasp something that always seemed just out of reach.

Despite the setbacks, Dylan’s resilience shone through. He understood that the creative process was often messy and unpredictable. It was in these moments of uncertainty that he learned the most about himself as an artist. While “Caribbean Wind” was ultimately set aside, it taught him valuable lessons about patience and perseverance. These experiences would later influence his remarkable album “Infidels,” where he explored new sounds and themes with renewed confidence.

In the end, “Caribbean Wind” never made it to the final cut, but it served as a stepping stone on Dylan’s journey. The song, although abandoned, held a special place in his heart. It reminded him that every artist faces obstacles and that not every creation will reach the audience. What truly mattered was the passion and dedication he poured into his work. Dylan’s story is a testament to the power of persistence in the face of failure. He continued to evolve, write, and inspire generations, proving that even the most legendary artists have moments of doubt and struggle. And through all of it, the music never truly stopped; it just kept flowing, much like the Caribbean wind he had once sought to capture.