Jason Mraz & Colbie Caillat, Lucky | Dazzling Duets

In the 20^th edition of Dazzling Duets (2025), Jason Mraz and Colbie Caillat collaborate on their Grammy-winning pop duet, “Lucky.” 

Sometimes, two is better than one! That is the case when it comes to Dazzling Duets! On Dazzling Duets, we highlight ear-catching songs performed by two artists collaborating. These duets can be from any musical style, making Dazzling Duets a flexible, versatile column on The Musical Hype. In the 20^th edition of Dazzling Duets (2025), Jason Mraz and Colbie Caillat collaborate on “Lucky.” Let the dazzle begin!

And the keyword is… lucky, of course! “Lucky” is the third track from We Sing. We Dance. We Steal Things., the 2008 multi-platinum album by Grammy-winning pop singer/songwriter Jason Mraz. On this Grammy-winning duet (Best Pop Collaboration With Vocals at the 52^nd Annual Grammy Awards), Mraz tapped the beautiful and talented Colbie Caillat for the assist. Mraz and Caillat penned “Lucky” with Timothy Fagan. Martin Terefe produced it.  While the duet didn’t quite make it to the top 40 of the pop charts, it peaked at number 48 on the Billboard Hot 100. In 2023, the single was certified quadruple platinum by the Recording Industry Association of America. Can you say, lucky?!

“Lucky” begins simply with a rhythmic guitar setting the tone. Later, the rest of the rhythm section helps fill out the musical accompaniment, in addition to warm strings. Jason Mraz draws first blood, performing the first half of the first verse radiantly. “Do you hear me? I’m talking to you,” he sings, and continues, “Across the water, across the deep blue ocean.” Colbie Caillat responds in the second half of the first verse: “Boy, I hear you in my dreams / I feel your whisper across the sea.” Their voices complement each other superbly.  The chemistry is top-notch during the chorus, excerpted earlier. The melodies are memorable from start to finish, particularly the chorus. Colbie Caillat leads the charge initially on the bridge, which distinguishes itself from everything else. Both singers take turns singing, as well as sing together on key moments such as “Waiting for a love like this,” and “I wish we had one more kiss / I’ll wait for you, I promise you, I will.”  Another iteration of the chorus precedes the second verse, which possesses a similar script to the first.  “You’ll hear the music fill the air / I’ll put a flower in your hair,” Mraz sings, to which Caillat responds, “As the world keeps spinning ‘round / You hold me right here, right now.” Ooh-wee! They join forces once more in the chorus, closing out “Lucky” with the outro filled with pure oohs.  All in all, Jason Mraz and Colbie Caillat recorded a duet for the ages, one that masterfully showcases their vocal and songwriting abilities.

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Jason Mraz » We Sing. We Dance. We Steal Things. » Atlantic Recording Corporation » 2008

Jason Mraz & Colbie Caillat, Lucky: Dazzling Duets No. 20 (2025) [📷: Brent Faulkner / The Musical Hype; Atlantic Recording Corporation; cottonbro studio, Sachith Ravishka Kodikara from Pexels; andresilva5, OpenClipart-Vectors from Pixabay]

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