Anita O’Day / Anita Sings Another Night / 2013
Taking a Chance on Love
buoyant, nervy optimism
This is a classic standard about surrendering to romance after resolving to avoid it, cast entirely through gambling imagery — cards, dice, numbers. Anita O'Day's reading leans into the song's rhythmic bounce and repetition to sell a mood of giddy, slightly breathless surrender rather than deep introspection.
risk and surrender renewed optimism love as a gamble self-persuasion joyful resignation
Who's speaking
A first-person speaker addresses no one directly but seems to be talking herself into belief, narrating her own change of heart in real time as it happens.
What happens
The song opens mid-motion, with the speaker already swept up again in a familiar rush of feeling she had sworn off. She then recalls her former skepticism — treating love as a rigged game not worth playing — before describing her reversal: she's now willing to bet, and the signs (a winning card, a rainbow) suggest the gamble will pay off. The song closes by repeating the title phrase like a mantra, as if the repetition itself is what convinces her.
How it's built
A standard AABA-ish popular song form: the opening stanzas establish the 'here I go again' refrain, a middle section narrates the backstory of resistance and reversal, and the ending dissolves into pure repetition of the hook, stripped of narrative, functioning almost like a vamp or outro tag that lets the vocalist play with the title phrase rhythmically.
Section by section
Opening verses
“here I go again”
The speaker enters already in motion, mid-relapse into feeling rather than at its start, which frames the song less as a decision than as an admission of a pattern repeating itself.
Middle narrative section
“the ace of hearts is high”
Here the gambling metaphor sharpens into specific card imagery, turning an abstract declaration of hope into something almost literal and visual, as if she's watching the odds turn in her favor.
Rainbow/happy ending lines
The imagery shifts briefly from gambling to a softer, almost folkloric symbol of reward, suggesting the speaker's optimism is expanding past the game metaphor into something more sentimentally assured.
Closing repetition
The lyric abandons further narrative development and simply loops the title phrase, a structural choice that mirrors the emotional state being described: she's no longer reasoning her way into the feeling, just repeating it until it becomes true.
Craft
- extended metaphor
- The entire lyric sustains a gambling conceit — cards, aces, numbers, bets — mapping romantic risk onto games of chance, which lets abstract emotional vulnerability be expressed in concrete, playful terms.
- anaphora
- Repeated openings like 'here I' and the recurring title phrase create a rolling, incantatory momentum that mimics the speaker talking herself into a decision.
- contrast/reversal
- The middle section sets up a before-and-after structure: former refusal to gamble versus present eagerness, dramatizing the moment of changed conviction.
Reading it
The most natural reading treats the song as a lighthearted, self-aware performance of romantic optimism — someone who knows love is a gamble and chooses it anyway, with the gambling conceit allowing wit rather than anxiety. A secondary reading could find a thinner vein of self-doubt beneath the cheerfulness, since the need to repeat the title so insistently hints that conviction is being built rather than simply felt. O'Day's performance style, built on rhythmic agility rather than vulnerability, tends to favor the first reading.
Context
"Taking a Chance on Love" is a 1940 standard (music by Vernon Duke, lyrics by John Latouche and Ted Fetter) long before O'Day's 2013 recording, which appears on a tribute/covers-style album of standards. I don't have reliable details about this specific session, its personnel, or its particular arrangement choices.
Listen for
- How she phrases the repeated title line differently each time it recurs, varying rhythm rather than melody
- Whether the tempo pushes forward during the gambling-imagery verses to suggest excitement
- The way the ending repetitions are handled vocally — scatted, clipped, or drawn out — since that choice colors whether the ending reads as triumphant or manic
- Any instrumental interplay (horns, rhythm section) that mirrors the 'trumpets blow again' imagery
About Anita O’Day
Anita O'Day was an American singer known for her work in the jazz genre. She was considered by writers an influential jazz vocalist for her ability to keep up with fast-tempo arrangements and for her characteristic vocal delivery.
1919 - 2006 / United States
Full biography and catalogue