The song "I'm Always Chasing Rainbows" by Perry Como explores themes of longing, frustration, and a constant pursuit for happiness that always seems out of reach. The lyrics convey a sense of perpetual struggle and disappointment in the narrator's life.

The opening line, "At the end of the rainbow there's happiness, and to find it how often I've tried," suggests that the narrator desires happiness and fulfillment, and has made numerous attempts to attain them. However, the following lines emphasize that the pursuit has been unsuccessful, describing life as "a race, just a wild goose chase" and asserting that dreams have been denied.

The repeated question, "Why have I always been a failure? What can the reason be?" reflects the narrator's introspection and self-doubt. They wonder if their struggles and failures are a result of external factors, questioning whether the world is to blame. Simultaneously, they also consider the possibility that their own actions or choices might contribute to their lack of success ("I wonder if it could be me?").

The phrase "always chasing rainbows" serves as a metaphor for the narrator's constant pursuit of happiness, often finding it just out of reach. The imagery of rainbows and drifting clouds represents fleeting moments of joy and positivity. However, the narrator's schemes and dreams ultimately "end in the sky," suggesting that they never materialize.

Comparisons are made to other people who seem to have better luck finding happiness and achieving success. Some "look and find the sunshine," while the narrator "always look[s] and find[s] the rain." This contrast highlights the narrator's perception of continually facing obstacles and setbacks compared to those who experience occasional victories.

The repeated line, "I'm always chasing rainbows, waiting to find a little blue bird in vain," further emphasizes the narrator's longing and frustration. The blue bird represents a symbol of hope or fulfillment, but the narrator acknowledges that their search is in vain, suggesting a resigning acceptance of their unsuccessful pursuit.

Overall, "I'm Always Chasing Rainbows" is a song that speaks to the universal human desire for happiness and fulfillment, while simultaneously expressing the challenges and disappointments that can come with that pursuit. It reflects on the narrator's repeated failures and the longing for the elusive happiness that seems to fade away, leaving them forever chasing rainbows.