Listening to Pandora stations shuffled off Turnpike Troubadours and Spotify suggestions based on a history centered around artists like Pat Green and Reckless Kelly, Toby Keith songs don’t come on very often. But recently when one did, I was reminded that some of Keith’s material is actually pretty good.  There’s a lot of Keith material to wade through, so here and for starters I’ll just focus on the period between 1993’s Toby Keith and 1999’s How Do You Like Me Now.  These albums I think bookend a distinct period in TK’s career that I’ll call the Early Years.

His eponymous first album included Should’ve Been a Cowboy and Wish I Didn’t Know Now, which are the two songs I’d label great off that album, and two of three great songs from the Early Years. Cowboy is a nostalgic romp through an idealized cowboy life replete with references to cowboys in American history, movies and music culture.  Wish I Didn’t is a heartbreak love song recounting Keith’s discovery of his girlfriend’s cheating and wishing nostalgically that they could start over together or at least that he could’ve continued in his pre-discovery ignorance.  Keith wrote both songs, and both are great for me because they’re centered around classic themes with relatively novel but not over-worked lyrics and deliveries that are believable and true to the style that Keith establishes in this album and carries forward over at least the next handful of albums.

Bookending the Early Years is How Do You Like Me Now, which was Keith’s breakout album and a signal of a different career direction, with Country Comes to Town, How Do You Like Me Now (the third great song from the Early Years) and the underrated Blue Bedroom which wasn’t released as a single. HDYLMN is an upbeat and fun song with a bit of cheek.  It’s a celebration of the narrator making it in the country business, looking back on the crush of his younger years who wouldn’t give him the time and contrasting this celebration with the less fortunate path that crush went down.  In this song (as a this point in his career) TK’s made it.  He’s in your ear on the radio as he turns his glance back and asks how you like him now, you as spurning girl and directed perhaps at the audience as well.

In between Toby Keith and HDYLMN there was some material that was solid, fine and OK and plenty that was forgettable. Off Boomtown I’d put You Ain’t Much Fun in the good category, it’s funny and pretty original.  And I’d put Who’s That Man in the fine category.  Blue Moon was mostly forgettable, and Dream Walkin’ redeemed with a couple good songs, including I’m So Happy I Can’t Stop Crying – written by Sting but delivered well by Keith – and the title track Dream Walkin’ whose vocals were extremely similar (in a good way) to Wish I Didn’t Know Now and whose lyrics were nice.

In the Early Years, TK was doing very well indeed. Four of his first five albums went platinum and his second four albums all cracked the Top 10 country charts, to be sure quite a feat for a new artist.  He also charted four number one singles, including the first release off Toby Keith Should’ve Been a Cowboy and the title track to HDYLMN, as well as 10 additional singles in the Top 10.  But chart success wasn’t automatic, as it would seemingly become in the Keith’s next period which I’ll call the Swagger Years.  Up until How Do You Like Me Now and Country Comes to Town, love was the predominant theme of Keith’s songs.  Most especially love songs with cheating, leaving, making mistakes, being replaced by another man, feelings of melancholy and loss, desperate, striving love and similar types of heartbreak and hard times love songs.  The minimal indications of vapid broiness in a few Early Years songs were more than offset by a broader corpus of thematically consistent songs with heartfelt lyrics, which it should certainly be noted were written or co-written in significant majority by Keith.  The next period, the Swagger Years, produced some of Keith’s best songs, but some questionable, wide misses too.