| Highwayman | Willie Nelson with Kris Kristofferson and Johnny Cash | | | 3:01 | |
| Highwayman | Willie Nelson, Kris Kristofferson, Shooter Jennings & Jamey Johnson | | | 3:11 | |
| Highwayman | Johnny Cash, Waylon Jennings, Willie Nelson & Kris Kristofferson | | | 3:04 | |
| Highwayman | J. Cash, Waylon Jennings, W. Nelson & K. Kristofferson | | | 3:04 | |
| Highwayman | Willie, Waylon, Cash & Kris | | | ?:?? | |
| Highwayman | Kris Kristofferson | | | 3:05 | |
| Hitting Close to Home | Kris Kristofferson | | | ?:?? | |
| Hitting Close to Home (demo) | Kris Kristofferson | | | 2:38 | |
| Hobo's Lullaby | Kris Kristofferson & Rita Coolidge | | | 5:02 | |
| Holy Creation | Kris Kristofferson | | | 4:38 | |
| Holy Woman | Kris Kristofferson | | | 2:29 | |
| Honey Come Back | Jimmy Webb feat. Kris Kristofferson | | | 4:11 | |
| Honky Tonk Heroes (Like Me) | Waylon Jennings, Billy Joe Shaver, Willie Nelson & Kris Kristofferson | | | 2:59 | |
| Hoola Hoop | Kris Kristofferson & Rita Coolidge | | | 3:52 | |
| Hoola Hoop | Kris Kristofferson & Rita Coolidge | | | 3:54 | |
| How Do You Feel (About Foolin’ Around) | Kris Kristofferson | | | 3:20 | |
| How Do You Feel About Foolin' Around | Kris Kristofferson with Willie Nelson | | | 2:48 | |
| How Do You Feel About Foolin' Around | Kris Kristofferson & Rita Coolidge | | | 3:47 | |
| How Do You Feel About Foolin' Around | Kris Kristofferson | | | ?:?? | |
| How Do You Feel About Foolin’ Around | Willie Nelson feat. Kris Kristofferson | | | 2:46 | |
| How Do You Feel About Foolin’ Around | Willie Nelson & Kris Kristofferson | | | 2:45 | |
| How Do You Feel About Foolin’ Around | Kris Kristofferson | | | ?:?? | |
| How Do You Feel About Foolin’ Around | Willie Nelson with Kris Kristofferson | | | 2:43 | |
| How Do You Feel About Foolin’ Around | Kris Kristofferson | | | 2:47 | |
| How Many Days | Kris Kristofferson | | | 3:21 | |
| I Believe That I Believe | Kris Kristofferson | | | ?:?? | |
| I Believe That I Believe (demo) | Kris Kristofferson | | | 2:44 | |
| I Can Be Had | Kris Kristofferson | | | ?:?? | |
| I Can Be Had (demo) | Kris Kristofferson | | | 2:33 | |
| I Couldn’t Be Me Without You | Waylon Jennings, Billy Joe Shaver, Willie Nelson & Kris Kristofferson | | | 2:02 | |
| I Do Believe | Kris Kristofferson | | | 3:27 | |
| I Do Believe | Kris Kristofferson | | | 3:33 | |
| I Do Believe | Kris Kristofferson | | | 3:33 | |
| I Fought the Law | Kris Kristofferson & Rita Coolidge | | | 2:28 | |
| I Fought the Law | Kris Kristofferson & Rita Coolidge | | | 2:25 | |
| I Fought the Law | Kris Kristofferson & Rita Coolidge | | | 2:40 | |
| I Got a Life of My Own | Kris Kristofferson | | | 3:37 | |
| I Got a Life of My Own | Kris Kristofferson | | | 3:38 | |
| I Got a Life of My Own | Kris Kristofferson | | | 3:37 | |
| I Got a Life of My Own | Kris Kristofferson | | | 3:34 | |
| I Got a Life of My Own | Kris Kristofferson | | | ?:?? | |
| I Hate Your Ugly Face | Kris Kristofferson | | | 1:26 | |
| I Hate Your Ugly Face | Rocket to Stardom & Kris Kristofferson | | | 2:16 | |
| I Heard the Bluebirds Sing | Kris Kristofferson & Rita Coolidge | | 3 | 2:48 | |
| I May Smoke Too Much | Kris Kristofferson | | | 3:09 | |
| I May Smoke Too Much | Kris Kristofferson | | | 3:06 | |
| I May Smoke Too Much | Kris Kristofferson | | | 3:09 | |
| I May Smoke Too Much (quad mix) | Kris Kristofferson | | | 3:09 | |
| I Never Had It So Good | Kris Kristofferson & Rita Coolidge | | 4 | 4:08 | |
| I Walk The Line | Brandi Carlile, Willie Nelson, Jamey Johnson, Shooter Jennings, Kris Kristofferson, Sheryl Crow, Amy Lee, Andy Grammer, Pat Monahan, Shelby Lynne, Iron & Wine, Carolina Chocolate Drops, Rhett Miller, Lucinda Williams, Buddy Miller & Ronnie Dunn | | | 2:29 | |
| I'd Rather Be Sorry | Kris Kristofferson & Rita Coolidge | | | 3:10 | |
| I'd Rather Be Sorry | Kris Kristofferson | | | 2:11 | |
| I'd Rather Be Sorry | Kris Kristofferson | | | ?:?? | |
| I'd Rather Be Sorry | Kris Kristofferson | | | ?:?? | |
| I'd Rather Be Sorry | Kris Kristofferson | | | 3:10 | |
| I'll Be Your Baby Tonight | Kris Kristofferson | | | 2:23 | |
| I'll Be Your Baby Tonight (Apr 22, 1973, Record Plant, Sausalito, CA) | Rita Coolidge & Kris Kristofferson | | | ?:?? | |
| I'll Be Your Baby Tonight (Live) | Willie Nelson & Kris Kristofferson | | | 3:05 | |
| I'll Be Your Baby Tonight (remastered) | Kris Kristofferson | | | 3:08 | |
| I'll Take Any Chance I Can With You | Kris Kristofferson | | | 3:29 | |
| I'm Down (But I Keep Falling) | Kris Kristofferson & Rita Coolidge | | 4 | 3:08 | |
| I've Got a Life of My Own | Kris Kristofferson | | | 3:38 | |
| I've Got To Have You | Kris Kristofferson | | | ?:?? | |
| I’d Rather Be Sorry | Kris Kristofferson feat. Rita Coolidge | | | 3:12 | |
| I’d Rather Be Sorry | Kris Kristofferson & Rita Coolidge | | 4 | 3:11 | |
| I’d Rather Be Sorry | Kris Kristofferson & Rita Coolidge | | | 3:13 | |
| I’ll Be Your Babe Tonight | Kris Kristofferson | | | 3:39 | |
| I’ll Be Your Baby Tonight | Kris Kristofferson | | | ?:?? | |
| I’ll Be Your Baby Tonight | Kris Kristofferson | | | ?:?? | |
| I’ll Be Your Baby Tonight | Willie Nelson, Kris Kristofferson | | | 2:56 | |
| I’ll Be Your Baby Tonight | Kris Kristofferson | | | 3:05 | |
| I’m Just an Old Chunk of Coal | Waylon Jennings, Billy Joe Shaver, Willie Nelson & Kris Kristofferson | | | 2:12 | |
| I’ve Got to Have You | Kris Kristofferson & Rita Coolidge | | 4 | 3:32 | |
| If It’s All the Same to You | Kris Kristofferson | | | 3:15 | |
| If You Don't Like Hank Williams | Kris Kristofferson | | | 3:30 | |
| If You Don't Like Hank Williams | Kris Kristofferson | | | 1:50 | |
| If You Don't Like Hank Williams | Kris Kristofferson | | | ?:?? | |
| If You Don’t Like Hank Williams | Kris Kristofferson | | | 3:31 | |
| If You Don’t Like Hank Williams | Kris Kristofferson | | | 3:30 | |
| If You Don’t Like Hank Williams | Kris Kristofferson | | | 3:30 | |
| If You Don’t Like Hank Williams | Kris Kristofferson | | | 3:31 | |
| If You Don’t Like Hank Williams | Kris Kristofferson | | | 3:32 | |
| If You Don’t Like Hank Williams | Kris Kristofferson | | | 3:32 | |
| If You Don’t Like Hank Williams (1968 demo) | Kris Kristofferson | | | 1:49 | |
| In the News | Kris Kristofferson | | | 3:31 | |
| Introduction | Kris Kristofferson | | | 0:56 | |
| Introduction | Lou Reed & Kris Kristofferson | | | 1:26 | |
| Introduction by Kris Kristofferson | Kris Kristofferson | | | 0:34 | |
| Introduction by Kris Kristofferson | Kris Kristofferson | | | 3:15 | |
| It No Longer Matters What I Do | Kris Kristofferson | | | 2:34 | |
| It Sure Was (Love) | Kris Kristofferson feat. Rita Coolidge | | | 2:54 | |
| It Sure Was (Love) | Kris Kristofferson | | | 2:53 | |
| It Sure Was (Love) | Kris Kristofferson | | | 3:36 | |
| It Sure Was (Love) (quad mix) | Kris Kristofferson | | | 2:57 | |
| It's All Over (All Over Again) | Kris Kristofferson & Rita Coolidge | | 4 | 2:45 | |
| It's All Over Now, Baby Blue | U2 feat. Van Morrison, Bob Dylan, Chrissie Hynde, Elvis Costello, Kris Kristofferson & Steve Winwood | | | 10:04 | |
| It's Never Gonna Be the Same Again | Kris Kristofferson | | | 3:55 | |
| It's Never Gonna Be the Same Again | Kris Kristofferson & Rita Coolidge | | | 3:47 | |
| It’s Never Gonna Be the Same Again | Kris Kristofferson | | | 3:54 | |
| It’s Never Gonna Be the Same Again | Kris Kristofferson | | | 3:54 | |
