Icon: The Best Of Vanessa Carlton, by Vanessa Carlton
There are a lot of people who have read what I have said about the career of Vanessa Carlton  and thought that I was not fond of her music. This is not quite true. This album represents probably the best possible sort of place to find Vanessa Carlton’s work, which has been nothing if not uneven. Vanessa Carlton has made some fantastic music–some of it, like her singles from Rabbits On The Run, are not even included here–but she has never made an album that can be enjoyed thoroughly all the way through. So, since she has made some great singles, it would make sense that her major label would release this best of collection for those who are fans of her more familiar work and not necessarily fans of her deeper album tracks. In short, this album was made with people like me in mind, for whom most of the songs are familiar and remembered fondly. A track-by-track review follows:
A Thousand Miles: This beautiful track will likely remind people of Vanessa Carlton’s career long after it is over. It is still beautiful even years after its debut with its girlish singing, its impassioned piano playing, and its earnestness. It is entirely fitting, therefore, that this lovely song should open this collection.
Ordinary Day: The second single off of Carlton’s debut album, this lovely song is one that I have always greatly enjoyed, and it was a successful hit as well, and likely a song that will be remembered in the future as well.
White Houses: The first single and by far the best song off of Carlton’s second album, this song was my favorite single of the year it came out. Too bad it barely hit the Hot 100, prompting Carlton’s rapid fall from commercial radio. This song is autobiographical in the best way, talking about Carlton’s time as a dance student struggling with the loss of innocence and the social world of the dancing community.
Heroes & Thieves: The title track of Vanessa Carlton’s commercially unsuccessful third album, this song has a story song feel to it. It has a somewhat uneven rhythm, but it’s a charming number with some lovely string flourishes, and deserves to be remembered. This is one of the treasures of Carlton’s back catalog.
Nolita Fairytale: The first single off of Vanessa Carlton’s third album, this song is one of my favorites of hers. The song combines Carlton’s familiar piano playing with a great beat and some thoughtful lyrics about troubles dealing with the record industry and learning to love a more downscale life.
Who’s To Say: One of the more obscure songs here, this song was taken from Vanessa Carlton’s second album. Listening to the song here, I like the song a lot better than I did when it was first released and I was disappointed with its spare instrumentation. This song seemed to prefigure the singer’s defiance of the opinions and judgments and standards of others that would mark her later career.
Home: A song taken from Vanessa Carlton’s third album, this song is a spare piano ballad about the singer’s desire for home. The song has a somewhat wistful tone, and makes for a sweet and lovely song reflecting the author’s desire for safety and security and love.
San Francisco: Probably the second best song off of Vanessa Carlton’s second album, this song was the only song other than “White Houses” I liked on initially listening to that album. Filled with lovely piano arpeggios, this is a love song for both co-writer Stephen Jenkins (of Third Eye Blind fame) and the city of San Francisco he comes from, another song that references Carlton’s desire for home and her finding it in transgressive places.
Pretty Baby: The third single of Vanessa Carlton’s first album, this song is a bit cloying and immature, about a cheating lover, sung a bit too melodramatically. There is a lot to enjoy in this song, but it definitely hasn’t worn as well as most of her other singles. It almost has to be included among her best of because of the fact that it was a hit, but all the same, she has done a lot better than this.
Hands On Me: The second single from Carlton’s third album, this song is a driving song about finding love in somewhat downscale circumstances, matching the general tone of that album’s first single. The song views romantic love in a context that is both somewhat threadbare–in the relationship making temp work worthwhile–and cosmic in nature, a fitting description of a common tension in her work. It’s a lovely song, though, and one of her best.
Twilight: This song from Carlton’s first album is pleasant enough album filler with a somewhat odd rhythm and spare piano instrumentation. The song, perhaps unkindly, plays like a track from the soundtrack to the eponymous movie, which is perhaps not the strongest point in its favor.
Private Radio: This song, from Carlton’s second album, is rather inoffensive album filler that uses its odd beat and quirky piano playing to make it sound more interesting. The song is unintentionally prophetic, though, in that Carlton rapidly tired of making beautiful pop songs and soon stopped being played on anything other than private radios. Good thing she prepared herself for that ahead of time.
This album gives a striking solution to the unevenness of Vanessa Carlton’s back catalog in that it provides the four best songs of each of her three major studio releases. Of course, the four best songs of her first and third albums are stronger than the best four songs of her second. Going forward, this album is likely to be the essential early Vanessa Carlton album. Why buy any of her three albums when this album has basically all of her good songs from those albums? The only way this album could be better given the constraints of its contents is if it added the four best songs of Rabbits On The Run, so that we could listen to “Carousel” or “I Don’t Want To Be A Bride” or “Hear The Bells” in addition to these ones.
 See, for example: