Year -- Song -- Highest Billboard Chart Position

Released Singles From Wide Open Spaces

1997 -- I Can Love You Better #7
1998 -- There's Your Trouble #1
1998 -- Wide Open Spaces #1
1998 -- You Were Mine #1
1999 -- Tonight The Heartache's On Me #5

Released Singles From Fly

1999 -- Ready To Run #2
1999 -- Cowboy Take Me Away #1
2000 -- Goodbye Earl #12
2000 -- Cold Day in July #9
2000 -- Without You #1
2001 -- If I Fall You're Going With Me #3
2001 -- Heartbreak Town #23
2001 -- Some Days You Gotta Dance #7                                                    

Released Singles From Home

2002 -- Long Time Gone (released 5/23/02) #4                                                    2002 -- Landslide (released 8/20) #28