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High Maintenance Woman: A Look Back at Toby Keith’s Single
Toby Keith’s “High Maintenance Woman” rolled onto the country music scene in February 2007. It served as the lead single for his eleventh studio album, “Big Dog Daddy.” The song, though credited solely to Keith, has an interesting backstory.

Keith actually wrote the core of the song himself, but he awarded co-writing credits to comedian Tim Wilson and his partner Danny Simpson. Why? Apparently, Wilson and Simpson had previously written a song with a similar theme. While the two songs weren’t directly connected, Keith felt their earlier work influenced his direction for “High Maintenance Woman,” and credited them accordingly.

Released in the wake of Keith’s mega-hit albums “Shock’n Y’all” and “Unleashed,” “High Maintenance Woman” took a lighter approach. The song is a good-natured look at the challenges and humorous realities of dating a woman with expensive tastes. While the lyrics might raise an eyebrow (or two), it’s delivered with a wink and a nudge, characteristic of Keith’s personality.

“High Maintenance Woman” became a Top 20 hit on the Billboard Hot Country Songs chart, reaching number 14. The accompanying music video, filmed in Miami, Florida, added a visual element to the song’s playful narrative.

So, as you hear the opening chords of “High Maintenance Woman,” remember its collaborative roots and its place in Toby Keith’s musical journey. It’s a song that injects a dose of fun into the often-serious world of country music, reminding us that sometimes, love comes with a hefty price tag (and a whole lot of laughter).

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