| Man of Constant Sorrow | Tony Furtado & Tim O’Brien | | | 4:11 | |
| Man of Constant Sorrow | Tony Furtado & Tim O’Brien | | | 4:11 | |
| Man of Constant Sorrow | Tony Furtado with Tim O’Brien | | | 4:08 | |
| Masters of War | Tim O’Brien | | 4 | 3:27 | |
| Me and Dirk's Trip to Ireland | Tim O’Brien | | | 2:36 | |
| Megna's | Tim O’Brien | | | 3:52 | |
| Melancholy Moon (Not) | Tim O’Brien | | | 3:51 | |
| Memories and Moments | Tim O’Brien and Darrell Scott | | | 3:35 | |
| Memories and Moments | Tim O’Brien & Darrell Scott | | | 4:04 | |
| Mick Ryan's Lament | Tim O’Brien | | | 3:21 | |
| Mick Ryan's Lament | Tim O’Brien & Darrell Scott | | | 3:38 | |
| Mole in the Ground | Dirk Powell, Tim O’Brien & John Herrmann | | | 3:02 | |
| Mom and Dad's Waltz | Tim O’Brien & Darrell Scott | | | 3:04 | |
| More Love | Tim O’Brien & Darrell Scott | | | 4:06 | |
| More Love | Tim O’Brien | | | 4:34 | |
| Moses | Tim O’Brien | | | 6:01 | |
| Mother Mary | Tim O’Brien | | | 3:02 | |
| Motherless Child | Tim & Mollie O’Brien | | | 3:49 | |
| Mountain Air / Washington's March / Bonaparte's Retreat | Dirk Powell, Tim O’Brien & John Herrmann | | | 5:02 | |
| Mountaineer Is Always Free | Tim O’Brien & Darrell Scott | | | 5:00 | |
| Mountaineers Are Always Free | Tim O’Brien | | | ?:?? | |
| Muswell Hillbilly | Tim O’Brien | | | 3:57 | |
| My Father's House | Tim O’Brien & Darrell Scott | | | 4:17 | |
| My Girl's Waiting for Me | Tim O’Brien | | | 4:05 | |
| My Girl's Waiting for Me | Tim O’Brien | | | 4:06 | |
| My Girl's Waiting for Me | Tim O’Brien | | | 4:12 | |
| My Love Lies in the Ground | Dirk Powell with Tim O’Brien | | | 3:16 | |
| My Love Lies In The Ground | Tim O’Brien | | | 3:13 | |
| My Old Brown Coat and Me | Tim O’Brien | | | 3:39 | |
| Nashville Blues | Robbie Fulks feat. Tim O’Brien | | | 3:30 | |
| Nellie Kane | Tim O’Brien | | | 3:26 | |
| Nellie Kane (feat. Hot Rize) | Tim O’Brien | | | 2:59 | |
| Nervous | Tim O’Brien | | | 3:02 | |
| No Way to Stop the Flow | Tim O’Brien | | | 3:25 | |
| Nobody's Fault but Mine | Tim & Mollie O’Brien | | | 3:13 | |
| Norwegian Wood | Tim O’Brien | | 3 | 4:06 | |
| Not Afraid o' Dyin' | Tim O’Brien | | | 4:45 | |
| Nothing To Say | Tim O’Brien | | | 3:44 | |
| Off My Mind | Cara Luft feat. Tim O’Brien | | | 3:38 | |
| Oh Come, O Come Emmanuel | Becky Buller feat. Tim O’Brien | | | 3:35 | |
| Oh Mama | Aoife O’Donovan with Mary Chapin Carpenter; Karen Matheson; Tim O’Brien; Julie Fowlis & Teddy Thompson | | | 4:07 | |
| Old Joe | Tim O’Brien | | | 3:42 | |
| Old Time River Man | Michael Cleveland feat. Tim O’Brien | | | ?:?? | |
| On Guitars, the Ends of New Fingers Get Sore | Tim O’Brien | | | 2:43 | |
| On Life's Other Side | Tim O’Brien and Darrell Scott | | | 4:00 | |
| On the Outside Looking In | Tim O’Brien | | | 4:07 | |
| One Drop of Rain | Tim O’Brien | | | 2:42 | |
| One Girl Cried | Tim O’Brien | | | 4:36 | |
| One Girl Cried | Tim O’Brien & Darrell Scott | | | 5:01 | |
| One Way Street | Tim O’Brien | | | 2:58 | |
| Origin Of Species | Tim O’Brien | | | 2:59 | |
| Orphan Girl | Tim & Mollie O’Brien | | | 3:48 | |
| Out in the Country | Tim & Mollie O’Brien | | | 5:15 | |
| Out in the Darkness | Tim O’Brien | | | 2:54 | |
| Out In The Darkness | Tim O’Brien | | | 2:49 | |
| Out on the Rolling Sea | Tim O’Brien | | | 4:07 | |
| Oxford Town | Tim O’Brien | | 3 | 1:55 | |
| Oxford Town (Mar 27, 2002, Canopy Club, Urbana, IL) | Tim O’Brien | | | ?:?? | |
| Paddy Fahey's / Garret Barry's / The Cliffs of Moher | Tim O’Brien | | | 5:22 | |
| Pagan Feast | Slavek Hanzlik & Béla Fleck, Tim O’Brien, Stuart Duncan, Mark Schatz | | | 3:58 | |
| Papa's on the Housetop | Tim & Mollie O’Brien | | | 2:49 | |
| Papa's on the Housetop | Tim & Mollie O’Brien | | | 3:05 | |
| Paradise | Tim O’Brien and Darrell Scott | | | 4:51 | |
| Paris Nights | Tim O’Brien, Bill Frisell & Dale Bruning | | | 4:13 | |
| Pastures Of Plenty | Tim O’Brien | | | 2:53 | |
| Pear Tree / Muddy Roads / Ladies' Pantelettes | Tim O’Brien | | | 3:38 | |
| Perfect Place to Hide | Tim O’Brien | | | 4:00 | |
| Perfect Place to Hide | Tim O'Brien And The O'Boys | | | 4:00 | |
| Phantom Phone Call | Tim O’Brien | | | 2:35 | |
| Pilgrim of Sorrow | Tim & Mollie O’Brien | | | 3:24 | |
| Pompadour | Tim O’Brien | | | 3:37 | |
| Poor Ellen Smith | Tim O’Brien | | | 2:23 | |
| Portland Town | Cara Luft feat. Tim O’Brien | | | 3:57 | |
| Pretty Fair Maid in the Garden | Tim O’Brien | | | 3:51 | |
| Price to Pay | Tim & Mollie O’Brien | | | 3:09 | |
| Pushing on Buttons (Staring at Screens) | Tim O’Brien | | | 4:15 | |
| Queen of Hearts | Tim O’Brien | | | 3:40 | |
| Queen of the Earth and Child of the Skies | Tim O’Brien | | | 3:33 | |
| Raleigh and Spencer | Dirk Powell, Tim O’Brien & John Herrmann | | | 2:44 | |
| Ready on the Firing Line | Tim O’Brien | | | 4:00 | |
| Red Dog in the Morning | Tim O’Brien | | | 2:40 | |
| Red Dog In The Morning | Tim O’Brien | | | 2:41 | |
| Red Rockin Chair | Tim O’Brien, Bill Frisell & Dale Bruning | | | 5:12 | |
| Red, White & Blues | Joe Troop feat. Tim O’Brien | | | 3:20 | |
| Reincarnation | O’Brien Party of 7 | | | 2:42 | |
| Remember Me | Tim & Mollie O’Brien | | | 3:33 | |
| Restless Spirit Wandering | Tim O’Brien | | | 5:03 | |
| Right Side of My Brain | Tim O’Brien & Darrell Scott | | | 2:30 | |
| River of Blood Nygaard | Tim O’Brien | | | 3:54 | |
| Rock in My Shoe | Tim O’Brien | | | 2:53 | |
| Rod McNeil | Tim O’Brien | | | 3:20 | |
| Romance Is A Slow Dance | Tim O’Brien | | | 3:34 | |
| Run Mountain | Tim O’Brien | | | 3:29 | |
| Run Mountain | Tim O'Brien And The O'Boys | | | 3:28 | |
| Runnin' Out of Memory | Tim O’Brien | | | 3:03 | |
| Runnin' Out of Memory | Tim O’Brien | | | 3:03 | |
| Safe In Your Arms | Tim O’Brien | | | 2:35 | |
| Sail Away | Tim O’Brien | | | 3:19 | |
| See You at the Funeral | Tim O’Brien | | | 4:02 | |
| Señor | Tim O’Brien | | | 4:01 | |
