Ten Prime Toby Keith Videos: A Man of Many Faces

Despite His Tough Guy Image, His Humor Always Shines Through

It would be an oversimplification to say that Toby Keith’s music videos show him evolving from a romantic golden boy to a glowering tough guy, but there is an element of that progression. And it’s not all due to the passing years. Much of it has to do with the tone of the songs at the center of these videos, which has gotten more cocky and less dreamy.

Ultimately, though, the videos demonstrate Keith’s complexity of character. He’s part scrapper, part boaster, part deep thinker and consistently a jokester. God love him.

Here are some of his video milestones:

“Should’ve Been a Cowboy” (1993) — You could get a whiplash watching Keith’s first and last videos back to back. In this debut effort, scenes of which are shot in the brownish tint of old movies, Keith is the complete romantic, imagining himself a fast-shooting, damsel-saving western hero. Mostly unhatted, immaculately dressed and with curls springing down to his shoulders, he is the very essence of boyish wish fulfillment. Nothing menacing here. His goals: “Stealing a young girl’s heart, just like Gene and Roy [and] singing those campfire songs.”

“Does That Blue Moon Ever Shine on You” (1996) — Heartsick at the love he’s pushed away, Keith stares wistfully out a rain-pelted window at night, wondering if his loneliness is reciprocated. He is still the young and handsome swain, sometimes staring into the distance, sometimes sitting on his bed and strumming his guitar. Oddly enough, the moon of the title never appears.

“How Do You Like Me Now?!” (1999) — This is where the nice, subdued chap of the earlier videos gives way to the triumphant score-settler every man dreams of being at one time or another. Keith invites the girl who once spurned him to meet him on the high school football field. Now she’s an unfulfilled, discontented housewife, and he’s a rising star. Guess who rubs it in — and take warning, all you heartless cheerleaders.

“Courtesy of the Red, White and Blue (The Angry American)” (2002) — Released after the invasion of Afghanistan and before the war started in Iraq, this video and song probably did more to solidify the public’s perception of Keith as a tough guy than anything else. Viewed from today’s perspective, with both wars still dragging on, the video’s heroic tone seems dated. Of course, that’s the fate of most topical art.

“Beer for My Horses” (2002) — Enjoy this one as a fully developed mini-movie. Keith is cast as a world-weary cop who, with his hapless sidekick, is trying to apprehend a serial killer. Having reached nothing but dead ends, he calls on the services of his father, a retired profiler played by Willie Nelson. Lots of action leavened with bits of overwrought whimsy.

“Who’s Your Daddy?” (2002) — Nobody touches Keith when it comes to leering, and that’s what he does here as he drives up to his mansion in an outrageously fancy truck, singing about his sugar-daddy access to disposable fluff. Naturally, his smirk disappears when he discovers that the bimbo who’s broken into his palatial digs has been lured there by his chubby groundskeeper, Cledus T. Judd.

“I Love This Bar” (2003) — Who wouldn’t love a bar that inspires one of its patrons to slip a beer bottle into her cleavage and then lean back and chug it down? In this one, Keith plays the bandleader who has to sing behind a chicken wire barrier and dodge the bottles hurled his way.

“American Soldier” (2003) — This is a much more subdued tribute to the military than “Courtesy of the Red, White and Blue.” There’s no drum beating, flag waving or muscle flexing — just a deep, calm appreciation of those who volunteer to risk their lives around the clock. The last scenes, with the wives and children staring through the fence as the troop planes fly away, are emotionally hard to take.

“Love Me If You Can” (2007) — This is Keith’s olive branch to those who’ve stereotyped him as a right-wing warmonger. Both the images and the lyrics of the song argue that he’s much more complex than that. His guitar case is emblazoned with stickers that shout many points of view from “Make Love, Not War” to “National Rifle Association” to “Got God?” Keith carries the video totally since he is the only figure you see. Stern and unsmiling, clad all in black and with dog tags swinging from his neck, he trudges into an apparently deserted TV station to make the statement, “Hate me if you want to/Love me if you can.” It’s one of his most intense and thought-provoking videos to date.

“God Love Her” (2008) — The attraction of good girls to bad boys is a recurring theme in country music. Here, a preacher’s daughter links up with a feckless “gypsy” motorcycle bum despite her parents’ pleas and warnings not to. In effect, she becomes his angel in residence by doing her own kind of missionary work. Instead of taking the role of the rider, Keith simply sings about his devilish appeal and good fortune. It’s a far cry from the wholesome faux cowboy who started it all.

Edward Morris is a veteran of country music journalism. He lives in Nashville, Tennessee, and is a frequent contributor to CMT.com.