John Mayer's 20 Best Songs: Critic's Picks

Billboard's most recent cover star John Mayer has been making music in the public eye for nearly 20 years. The singer-songwriter has won seven Grammys, scored the most No. 1s on Billboard's Top Rock Albums chart of any artist (7), and notched 20 Hot 100 hits.

Adult pop-rock is his bread and butter, and in his own words, “I don’t make music for the club. I make music for the omelette on the Sunday after the club" -- a time when we’re all the most honest with ourselves.

The essence of John Mayer’s music is honest, nostalgic and raw. It is metaphorical yet direct. John Mayer makes music that describes what you’re going through, even if you don’t realize you’re going through something. He finds the metaphors and analogies that help life make sense, even when it doesn’t. 

Below, Billboard ranks John Mayer's 20 best songs. 

20. "Why Georgia" (Room for Squares, 2001)

Off Mayer’s 2001 debut album, Room for Squares,’“Why Georgia” is an upbeat ode to coming of age and carving your own path. The song also gives us a preview of his effortless ability to toss unusual words into pop songs without sounding forced: “Either way I wonder sometimes about the outcome of a still verdictless life.” 

19. "Waiting on the World to Change" (Continuum, 2006)

Releasing a mildly politically charged song was definitely a power move for John Mayer with his Continuum lead single, but the song is something of an anti-anthem -- while Mayer sings about waiting, the purposeful lack of urgency in his lyrics and vocals carries throughout the song. “Waiting on the World to Change” won the Grammy for Best Male Pop Vocal Performance in 2006. 

18. "Vultures" (Continuum, 2006)

Mayer’s vocal range in “Vultures” is what makes the song so great. Traditionally known for his velvety, smooth voice, so when he actually flexes on a couple high notes, you can't help but notice. With bold metaphors layered over funky piano and searing guitar solos, “Vultures” is quintessential John Mayer. 

17. "Clarity" (Heavier Things, 2003)

“Clarity” was the second single off 2003’s Heavier Things, and it did not disappoint. With smooth horns by the recently passed Grammy-winner Roy Hargrove, drums and piano by Roots legend Questlove, and Mayer’s infectious “ooOOooh, ooOOooh” sighs before each chorus, the song comes together for easy-listening perfection. 

16. "Gravity" (Continuum, 2006)

“Gravity” is the perfect song for when you’re in your feelings. Here, we see John Mayer’s blues at the forefront of the song, keeping the singing to a minimum in favor of a heavy guitar solo -- you can hear more of the pain and emotion in Mayer's guitar than in his vocals. The artist himself seems to have a great deal of fondness for the song -- he’s released it on three separate albums, and it won the Grammy for best solo rock vocal the third time out as a live version on 2008's Where the Light Is: John Mayer Live in Los Angeles.

15. "Edge of Desire" (Battle Studies, 2009)

John Mayer has a way of saying things one might be ashamed of and making them sound beautiful; in this case, “I want you so bad I'll go back on the things I believe.” “Edge of Desire” questions how far you’ll go for love. His raw honesty crescendos to the point where he’s practically screaming, begging at the end of the track. The song also includes perhaps one of Mayer’s most creative lyrics: “Maybe this mattress will spin on its axis and find me on yours.”

14. "Bigger Than My Body" (Heavier Things, 2003)

A feel-good song through and through, the prominent drums and bouncy guitar carry the track. Mayer also shares the sentiment that the best is yet to come: You’re capable of way more than what you or anyone else gives you credit for, and Mayer gets the message across without being cheesy or preachy. 

13. "No Such Thing" (Room For Squares, 2001)

“No Such Thing” is the debut single that John Mayer burst onto the scene with, peaking at No. 13 on the Billboard Hot 100 and enduring as one of his signature hits. It’s the first of many time we hear Mayer sing of his parents and their inevitable aging, which he returns to on later albums. But the final takeaway of the track is about not taking yourself too seriously, while also not selling yourself short: “I’d like to think the best of me is still hiding up my sleeve.”

12. "Your Body Is a Wonderland" (Room For Squares, 2001)

Mayer’s second career single peaked at No. 18 on the Hot 100, but more importantly, it was the first time America realized he could be seductive. With lines like “One mile to every inch of your skin like porcelain,” and his repetition of “I’ll use my hands,” John Mayer brought sex appeal to this acoustic ballad without making it feel dirty. 

11. "Who Says" (Battle Studies, 2009)

“Who Says” is 100 percent an IDGAF song -- albeit a fairly gentle one. It’s a middle finger to the naysayers, but Mayer’s smooth voice delivers the message inoffensively. The opening line “Who says I can’t get stoned?” gave Mayer an edge and a cool factor that he now exudes effortlessly. 

10. "Love on the Weekend" (The Search For Everything, 2017)

This song is all about the simple pleasure of spending the weekend with the one you love. While most of Mayer’s best songs have a melancholy romanticism about them, this song is the opposite: He mixes simple sentiments like “I can’t believe I get to see your face” with signature multi-syllable surprises in the sweet lyrics, treating the listener to lines like “And I’ll be dreaming of the next time we can go into another serotonin overflow" -- which automatically make you crave higher serotonin levels, something you’ve probably never thought about. What other pop song can say the same? 

9. "The Heart of Life" (Continuum, 2006)

Sometimes, John Mayer’s voice is so lovely that it’s not hard to get whisked away by the sound. However, “The Heart of Life” is one of those songs that will make you emotional if you listen to the words -- filled with lyrics like “Bad news never has good timing,” which basically amount to “It be like that sometimes.” The one liner “The heart of life is good” will instantly fill you with gratitude, no matter how complicated life can be.

8. "You’re Gonna Live Forever In Me" (The Search For Everything, 2017)

The whistling at the introduction practically hits you over the head with nostalgia. It brings you to simpler times, and you just know it’s going to be something wholesome. You can hear and feel Mayer’s raw emotion as he sets up behind the piano this time, rather than his usual six-string, and as a listener you can’t help but adopt the same feelings. 

7. "Daughters" (Heavier Things, 2003)

No one but John Mayer can make a song accusing a woman of having daddy issues sound so damn beautiful. Mayer’s recurring theme of how our parents affect our lives is carried through the song with folk-y guitar strums and gentle percussion. “Daughters” won the Grammy for song of the year in 2005, and it’s easy to see why.

6. "Emoji of a Wave" (The Search For Everything, 2017)

Mayer’s song title for this track is super new-school, but the message is as classic as ever. This time, the singer-songwriter likens hardships in life and relationships to the cyclic nature of waves: They come and go, and you just have to accept them to get through it. The strings in the background really elevate the song to a new level, and the lyric "Your heart is where my head should be, the dissonance is killing me" is quintessential Mayer. 

5. "New Light" (Non-album single, 2018)

“New Light” ushers in a new era of John Mayer in many ways. For one, we hardly ever hear the singer pining for a lover, and especially not while stuck in the friend-zone. The funky single, co-written and produced by No. I.D., showcases a sound that Mayer has been working on over the last few years by collaborating with artists from all corners of the industry -- Shawn Mendes and Travis Scott to name a couple -- and the result is sonically unlike any other song in his catalog, but the mid-song guitar solo still brings us back to classic John Mayer. 

4. "Half of My Heart" (Battle Studies, 2009)

By the time this song was released, Mayer had earned a reputation as something of a player. This song addresses that persona, but softens the blow by acknowledging that it takes two to make a tabloid romance. Mayer and famed eventual-ex Taylor Swift’s voices harmonize so well together that they sound like they were meant to be as one on the track. Mayer apparently felt the same way, revealing in a since-deleted tweet that Swift “would make a killer Stevie Nicks to my [Tom] ‘Petty’ of a song.” The harmonies between the two and piercing guitar riffs make for a perfectly-balanced hit, earning the hit single a Grammy nomination for best male vocal pop performance in 2010. 

3. "Stop This Train" (Continuum, 2006)

“Stop This Train” addresses the anxieties we feel about growing up directly, by using a train as a metaphor for life. It’s a very, very real feeling that twenty-somethings often have trouble vocalizing -- short of annoying words like “adulting” -- but that’s why we have John Mayer to do it for us. He reflects on his own life, while again referencing his parents in a very blunt aspect of life we all must face: “Don’t know how else to say it, don’t want to see my parents go.”  

2. "Free Fallin’" (Where the Light Is: John Mayer Live in Los Angeles, 2008)

Mayer’s cover of Tom Petty’s 1989 classic “Free Fallin’,” released as part of his Where the Light Is live set, does complete justice to the incomparable original, but also breathes new life into the song by switching up the song's melodies. Mayer’s vocal range gets the spotlight on the chorus, emphasizing the “singer” part of his usual "singer-songwriter" billing. Just as he did with his cover of Beyonce’s “XO" -- both of which perennially rank among his top-streamed songs on Spotify -- he manages to make a Tom Petty song into a John Mayer song.

1. "Slow Dancing In a Burning Room" (Continuum, 2006)

“Slow Dancing in a Burning Room” is the ultimate John Mayer Song. “Slow dancing in a burning room” might be one of his most poignant metaphors, the imagery beautiful yet chaotic. The song brings layers of intimacy, from its lyrics to its slow-cooked groove, that set it apart even from his other best songs. Lines like “You'll be a bitch because you can” are out of character for the singer, making the lyric that much more memorable. "Slow Dancing" takes a reverse format from many of his other most famous songs, ending with a series of questions (“Don’t you think we oughta know by now?”) rather than posing them from the outset. 

As a recorded highlight of 2006's Continuum, the song is great, but when it’s played live, it’s an experience. Watching Mayer play the song in person is to see an artist truly immersing himself in his craft, and as a spectator it’s mesmerizing to watch. There’s no saying how long he’ll extend the guitar solo, or in which direction he’ll take it. John Mayer takes live music to a whole new level, and it’s one of the reasons why he’s being honored at Billboard’s Live Music Summit on Nov. 13-14.