Entertainment Music Toby Keith - The Singles Print Google Images/blogs.sacbee.com Music Country Music Top Artists Top Picks Rock Music Pop Music Alternative Music Classical Music Folk Music Rap & Hip Hop Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Shelly Fabian Updated on 06/03/19 Toby Keith has consistently churned out great music since his 1993 debut with the release of his first single and No. 1 hit, "Should've Been a Cowboy." Keith has a whopping 20 No. 1 singles under his belt. This list compiles all of his charting singles*, including their original albums. Toby Keith Singles These rankings are from the Billboard Hot Country Songs charts. *As of October 2, 2015. Toby Keith (1993) "Should've Been a Cowboy" (No. 1)"He Ain't Worth Missing" (No. 5)"A Little More Talk and a Lot More Action" (No. 2)"Wish I Didn't Know Now" (No. 2) Boomtown (1994) "Who's That Man" (No. 1)"Upstairs, Downtown" (No. 10)"You Ain't Much Fun" (No. 2)"Big Ol' Truck" (No. 15) Christmas to Christmas (1995) "Santa, I'm Right Here" (No. 50) Blue Moon (1996) "Does That Blue Moon Ever Shine On You?" (No. 2)"A Woman's Touch" (No. 6)"Me Too" (No. 1) Dream Walkin' (1997) "We Were in Love" (No. 2)"I'm So Happy That I Can't Stop Crying" (No. 2)"Dream Walkin'" (No. 5)"Double Wide Paradise" (No. 40) Greatest Hits, Vol. 1 (1998) "Getcha Some" (No. 18)"If a Man Answers" (No. 44) How Do You Like Me Now?! (1999) "When Love Fades" (No. 44)"How Do You Like Me Now?!" (No. 1)"Country Comes to Town" (No. 4)"You Shouldn't Kiss Me Like This" (No. 1) From the compilation album A Country Christmas 2000 (2001) "Old Toy Trains" (No. 57) Pull My Chain (2001) "I'm Just Talkin' About Tonight" (No. 1)"I Wanna Talk About Me" (No. 1)"My List" (No. 1)"I Can't Take You Anywhere" (No. 24) Unleashed (2002) "Courtesy of the Red, White and Blue (The Angry American)" (No. 1)"Who's Your Daddy?" (No. 1)"Rock You Baby" (No. 13)"Beer for My Horses" (No. 1) Shock 'n Y'all (2003) "I Love This Bar" (No. 1)"American Soldier" (No. 1)"Whiskey Girl" (No. 1) From the Jimmy Buffet album License to Chill (2004) "Hey Good Lookin'" feat. Clint Black, Kenny Chesney, Alan Jackson, Toby Keith and George Strait (No. 8) Greatest Hits 2 (2004) "Stays In Mexico" (No. 3)"Mockingbird" (No. 27) Honky Tonk University (2005) "Honky Tonk U" (No. 8)"As Good As I Once Was" (No. 1)"Big Blue Note" (No. 5) White Trash With Money (2006) "Get Drunk and Be Somebody" (No. 3)"A Little Too Late" (No. 2)"Crash Here Tonight" (No. 15) Big Dog Daddy (2007) "High Maintenance Woman" (No. 3)"Love Me If You Can" (No. 1)"Get My Drink On" (No. 11) A Classic Christmas (2007) "Rockin' Around the Christmas Tree" (No. 44)"Winter Wonderland" (No. 55)"Let It Snow, Let It Snow, Let It Snow" (No. 53)"Little Drummer Boy" (No. 41) 35 Biggest Hits (2008) "She's a Hottie" (No. 13) That Don't Make Me A Bad Guy (2008) "She Never Cried In Front of Me" (No. 1)"God Love Her" (No. 1)"Lost You Anyway" (No. 10)"That Don't Make Me A Bad Guy" (No. 60) American Ride (2009) "American Ride" (No. 1)"Cryin' for Me (Wayman's Song" (No. 6)"Every Dog Has Its Day" (No. 15) Bullets in the Gun (2010) "Trailerhood" (No. 19)"Bullets in the Gun" (No. 12)"Somewhere Else" (No. 12) Clancy's Tavern (2011) "Made In America" (No. 1)"Red Solo Cup" (No. 9)"Beers Ago" (No. 6) Hope On the Rocks (2012) "I Like Girls That Drink Beer" (No. 18)"Hope On the Rocks" (No. 29) Drinks After Work (2013) "Drinks After Work" (No. 28)"Shut Up and Hold On" (No. 49) 35 MPH Town (2015) "Drunk Americans" (No. 33)