Every #1 Single of the Nineties: Toby Keith, “Wish I Didn’t Know Now”

“Wish I Didn’t Know Now”

Toby Keith

Written by Toby Keith

Radio & Records

#1 (1 week)

May 20, 1994

Another timeless recurrent from Toby Keith.

The Road to No. 1

Toby Keith followed his No. 1 debut single “Should’ve Been a Cowboy” with the top five “He Ain’t Worth Missing” and the top ten “A Little Less Talk (and a Lot More Action).”  The fourth and final single from Toby Keith returned him to the top.

The No. 1

I remember this getting a negative review in Billboard when it was released.  It didn’t make sense to me then and it still doesn’t make sense to me now.  I think this song is borderline genius.

It captures the moment of realization that you’ve been being lied to all along, but takes the emotional reaction in a different direction than expected. This guy wishes to go back to blissful ignorance, even though he’s “sure found out too much to stay.”

Keith is so damn good at rugged vulnerability, and this is one of his best demonstrations of that dichotomy.  Staying with the woman who humiliated him isn’t an option, but he’s still going to deeply miss the illusion he was living under.

“Please don’t say you’re sorry,” he asks.  “I just might stay another day.”

The Road From No. 1

Toby Keith’s lead single from his sophomore album will follow this to No. 1, and it’s a winner, too.

“Wish I Didn’t Know Now” gets an A.

Every No. 1 Single of the Nineties

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  1. This is probably my absolute favorite Toby Keith song. I am not too keen on what he’s been doing for the last 20 years but his pre-HDYLMN music very good.

  2. This is a great example of Keith’s skill as a songwriter. Keith has always had this special ability to upend expectations with his word play and sequencing of lyrics. That’s not to see he couldn’t also be as a direct as a boot in your ass.

    He is underappreciated as a tune-smith primarily because he became such a polarizing political figure; he was easy to stereotype and was often caricatured and dismissed. I think I have had to be an apologist for Toby Keith’s music more than any other contemporary country artist.

    I agree that his first four albums are very good with “Dream Walking” as perhaps the best, but I think the same case can be made for his work post 1999. Even as the singles continued to play to a type, every album had several amazing deep cuts. The persona Keith adopted all but guaranteed that made him a bad guy in the eyes of critics and the non-country audience.

    This songs demands you listen to it to make sure you sort out whay is happening, but when you do it just clicks.

    Oh, and Toby Keith can flat out sing.

  3. I didn’t get Toby during his chart topping todays. I now realize that was my fault. I was getting so frustrated with country radio at this time I wasn’t paying attention to the lyrics. Since then I have listened to more Toby and I now realize what a great songwriter he is. His songwriting reminds me of Bill Anderson’s. Just great observations of real life

  4. To be fair, Toby *could* flat out sing, but those days are long gone. Just in terms of what he released last year as singles, both the aptly-named “The Worst Country Song of All Time”, as well as “Old School”, are unlistenable.

    This song is my favorite of his, however.

  5. Yes, I love this song, and it’s still one of my all time favorites from Toby Keith! As I mentioned all the way back in the “Should’ve Been a Cowboy” entry, I love Harold Shedd and Nelson Larkin’s production on Toby’s debut album, and this song is just perfectly produced. I’ve always loved the sound of the drums, the guitar work, and the lovely steel playing throughout the second verse, especially. To me, this is one of the few early 90’s sounding records that was thankfully still able to have success in the middle of 1994, AND have a long recurrent life after its chart run. Oh, and I love how relatable it is lyrically, as well. How many of us at one time or another have wished that we “didn’t know now what we didn’t know then”?

    Because I wasn’t really listening to country radio in 1994, I never heard the most of these last several entries during their original chart runs. However, I actually remember hearing this one on at least a couple of occasions in 1994 when I was riding in the car with my dad. And I remember for some reason thinking it was either Brooks & Dunn or Lee Roy Parnell whenever I heard it. Of course, I still had no clue who Toby Keith was back then. I remember really liking the song, though. I quickly became familiar with Toby when I finally got back into country radio in 1995 and 1996, though, and this was another one of the recurrents from him that I’d hear very often. It remained a steady recurrent for us going into the early 00’s, and I always really enjoyed it whenever it came on.

    Actually, one thing I always found pretty impressive about Toby’s debut is how all four singles managed to have a very long shelf life on the radio. I also really love “He Ain’t Worth Missing” especially, and I could’ve sworn that was also a number one.

    I also agree with Peter that Toby’s output remained pretty solid throughout the 90’s and early 00’s (I also LOVE the Dream Walkin’ album), though I personally think he started slipping a bit around the Unleashed era and especially the Shockin’ Y’all era. The album after that, Honky Tonk University, has a lot of excellent album cuts, though.

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