High Maintenance Woman

Although Keith was technically the sole writer of "High Maintenance Woman," he gave co-writers' credit to comedian and singer Tim Wilson and Danny Simpson (Wilson's frequent co-writing partner), largely because Wilson and Simpson had previously composed together an unrelated song that also contained a similar premise. On his official website, Keith states:

I got to the studio and played ["High Maintenance Woman"] for the session guys and they said, "Aw, man. There's a comedian named Tim Wilson who's got a skit about that and has a little ditty song that's kind of the same thing."… Tim's a friend of mine, so I called him and told him about my song… I said I wouldn't even record mine without his blessing, which he gave. And just because I don't want anyone to ever think I copped his song, we threw him a small share of the writing and put their names on it.[1]

The song tells of an apartment-building maintenance man who is attempting, and failing, to attract the attention of an attractive woman who lives in an apartment in the complex, and lamenting that "a high-maintenance woman don't want no maintenance man". In colloquial usage predating Keith's use of the term, a "high maintenance woman" is a woman regarded as overly demanding or fussy.

Kevin John Coyne, reviewing the song for Country Universe, gave it an A- rating. Despite the story being told many times before and containing a "jaw-droppingly tacky double entendre", Coyne called it "a fantastic single" due to its writing and Keith's vocal performance.[2] Kathi Kamen Goldmark of Common Sense Media praised the song's lead guitar and rhythm section for emitting catchy energy and the "memorably clever" lyricism.[3] Entertainment Weekly writer Ken Tucker highlighted this and "Wouldn't Wanna Be Ya" for their clever vocalization and wordplay.[4]

The music video was directed by Michael Salomon and was released in early 2007. The guitar used in the video was a custom made Rockit Guitar built by Rod "Hot Rod" MacKenzie.

"High Maintenance Woman" debuted at number 73 on the Billboard Hot 100 the week of March 3, 2007.[5] Thirteen weeks later, it reached number 67 the week of June 2 and left the chart two weeks later.[6] The song reappeared on the Hot 100 the week of June 30 at number 100 before leaving completely,[7] staying on the chart for seventeen weeks.[8] In Canada, the song debuted at number 78 on the Canadian Hot 100 the week of March 31.[9] Six weeks later, it peaked at number 50 the week of May 12, remaining on the chart for thirteen weeks.[10]

• Lyrics of this song at MetroLyrics