"High Maintenance Woman" is a song co-written and recorded by American country music artist Toby Keith. It was released in February 2007 as the lead-off single from Toby's album Big Dog Daddy. The song reached a peak of number 3 on the country charts in mid-2007. Keith wrote the song single-handedly with additional writing credit to Tim Wilson and Danny Simpson.

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.

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.

Kevin John Coyne, reviewing the song for Country Universe, gave it a A- rating. He said that even though "the plotline is ripped off" and it contains a "jaw-droppingly tacky double entendre about having all the right tools, it is a fantastic single." He then goes on to say that "the song is well-written and his performance is top-notch."

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.

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Wikipedia