| 1 | Hold Your Head Up | Cover | Argent | 538 | 313 | Aug 21, 1987 | Jul 29, 2023 |
| 2 | Also Sprach Zarathustra | Cover | Strauss, as interpreted by Deodato | 279 | 276 | Jul 16, 1993 | Apr 16, 2026 |
| 3 | Ya Mar | Cover | Cyril Ferguson | 239 | 239 | Feb 21, 1987 | Apr 24, 2026 |
| 4 | Funky Bitch | Cover | Son Seals | 238 | 238 | Dec 6, 1986 | Sep 20, 2025 |
| 5 | Good Times Bad Times | Cover | Led Zeppelin | 231 | 231 | Dec 6, 1986 | Sep 14, 2025 |
| 6 | Uncle Pen | Cover | Bill Monroe | 213 | 213 | Mar 28, 1990 | Aug 5, 2017 |
| 7 | Rocky Top | Cover | Osborne Brothers | 207 | 207 | Sep 21, 1987 | Jul 23, 2025 |
| 8 | Sweet Adeline | Cover | Artie Shaw | 177 | 177 | Mar 28, 1990 | Dec 29, 2016 |
| 9 | Back on the Train | Cover | Trey Anastasio | 175 | 173 | Jun 24, 1999 | May 2, 2026 |
| 10 | Sand | Cover | Trey Anastasio | 164 | 163 | Sep 11, 1999 | May 1, 2026 |
| 11 | Loving Cup | Cover | The Rolling Stones | 156 | 156 | Feb 3, 1993 | Jan 31, 2026 |
| 12 | Backwards Down the Number Line | Cover | Trey Anastasio | 148 | 148 | Mar 6, 2009 | Apr 23, 2026 |
| 13 | First Tube | Cover | Trey Anastasio | 148 | 147 | Sep 9, 1999 | Apr 25, 2026 |
| 14 | Fire | Cover | Jimi Hendrix Experience | 138 | 138 | Dec 1, 1984 | Jul 25, 2023 |
| 15 | Light | Cover | Trey Anastasio | 137 | 135 | May 31, 2009 | Apr 17, 2026 |
| 16 | Take the 'A' Train | Cover | Duke Ellington | 122 | 122 | Apr 29, 1987 | Apr 13, 1994 |
| 17 | Cities | Cover | Talking Heads | 117 | 111 | Dec 1, 1984 | Apr 25, 2026 |
| 18 | Amazing Grace | Cover | Traditional | 113 | 110 | Jan 28, 1993 | Oct 3, 1998 |
| 19 | Timber (Jerry the Mule) | Cover | Josh White and Sam Gary | 109 | 109 | Apr 29, 1987 | Apr 25, 2026 |
| 20 | Jam | Cover | Traditional | 108 | 93 | Nov 3, 1984 | Jan 27, 2026 |
| 21 | Gotta Jibboo | Cover | Trey Anastasio | 108 | 107 | Sep 10, 1999 | Apr 16, 2026 |
| 22 | My Soul | Cover | Clifton Chenier | 101 | 101 | Feb 13, 1997 | Apr 25, 2026 |
| 23 | Boogie On Reggae Woman | Cover | Stevie Wonder | 98 | 98 | Feb 21, 1987 | May 1, 2026 |
| 24 | Rock and Roll | Cover | The Velvet Underground | 97 | 97 | Oct 31, 1998 | May 1, 2026 |
| 25 | Love You | Cover | Syd Barrett | 96 | 93 | Oct 31, 1987 | Jul 16, 2016 |
| 26 | Frankenstein | Cover | The Edgar Winter Group | 95 | 94 | Nov 11, 1989 | May 2, 2026 |
| 27 | Walk Away | Cover | The James Gang | 93 | 93 | Jul 23, 1988 | Apr 18, 2026 |
| 28 | Paul and Silas | Cover | Josh White | 92 | 92 | Sep 13, 1990 | Jun 24, 2025 |
| 29 | Peaches en Regalia | Cover | Frank Zappa | 89 | 89 | Oct 15, 1986 | Sep 16, 2025 |
| 30 | Golden Age | Cover | TV on the Radio | 89 | 89 | Nov 27, 2009 | Apr 23, 2026 |
| 31 | Ginseng Sullivan | Cover | Norman Blake | 87 | 87 | Aug 11, 1993 | Sep 14, 2025 |
| 32 | Sneakin' Sally Thru the Alley | Cover | Lee Dorsey | 87 | 86 | Mar 8, 1985 | Apr 30, 2026 |
| 33 | Cold as Ice | Cover | Foreigner | 85 | 48 | Jan 14, 1992 | May 18, 1992 |
| 34 | Bold As Love | Cover | Jimi Hendrix Experience | 85 | 85 | Jul 7, 1988 | Jun 21, 2025 |
| 35 | Carolina | Cover | Traditional | 85 | 85 | Jan 20, 1990 | Jul 12, 2025 |
| 36 | Avenu Malkenu | Cover | Traditional | 84 | 84 | May 11, 1987 | Apr 21, 2022 |
| 37 | Jesus Just Left Chicago | Cover | ZZ Top | 82 | 82 | Aug 10, 1987 | Jul 12, 2025 |
| 38 | La Grange | Cover | ZZ Top | 82 | 82 | Aug 9, 1987 | Jul 8, 2012 |
| 39 | Highway to Hell | Cover | AC/DC | 77 | 77 | Oct 1, 1989 | Aug 16, 2009 |
| 40 | Nellie Kane | Cover | Hot Rize | 76 | 76 | Feb 23, 1993 | Jul 3, 2025 |
| 41 | When the Circus Comes | Cover | Los Lobos | 76 | 76 | Feb 13, 1997 | Jul 11, 2025 |
| 42 | A Day in the Life | Cover | The Beatles | 75 | 75 | Jun 10, 1995 | Sep 12, 2025 |
| 43 | Everything's Right | Cover | Trey Anastasio | 74 | 73 | Jul 14, 2017 | Apr 16, 2026 |
| 44 | Crosseyed and Painless | Cover | Talking Heads | 74 | 71 | Oct 31, 1996 | May 1, 2026 |
| 45 | Terrapin | Cover | Syd Barrett | 67 | 66 | Sep 21, 1987 | Dec 4, 2019 |
| 46 | Hello My Baby | Cover | Howard and Emerson | 57 | 57 | Sep 27, 1995 | Dec 3, 2019 |
| 47 | Beauty of My Dreams | Cover | The Del McCoury Band | 57 | 57 | Feb 16, 1997 | Jul 4, 2025 |
| 48 | Roses Are Free | Cover | Ween | 53 | 53 | Dec 11, 1997 | Jul 27, 2025 |
| 49 | Cracklin' Rosie | Cover | Neil Diamond | 52 | 52 | Jan 14, 1992 | Jul 29, 2023 |
| 50 | The Old Home Place | Cover | The Dillards | 51 | 51 | Jun 26, 1994 | Sep 13, 2025 |
| 51 | Sigma Oasis | Cover | Trey Anastasio | 50 | 49 | Dec 8, 2019 | Apr 18, 2026 |
| 52 | Whipping Post | Cover | The Allman Brothers Band | 49 | 49 | Nov 3, 1984 | Jul 25, 1999 |
| 53 | Drowned | Cover | The Who | 48 | 48 | Oct 31, 1995 | Oct 15, 2023 |
| 54 | The Ballad of Curtis Loew | Cover | Lynyrd Skynyrd | 48 | 48 | Apr 29, 1987 | Dec 30, 2019 |
| 55 | My Mind's Got a Mind of its Own | Cover | Jimmie Dale Gilmore | 47 | 47 | Jan 14, 1992 | Jul 11, 2025 |
| 56 | Ruby Waves | Cover | Trey Anastasio | 46 | 42 | Jun 18, 2019 | May 2, 2026 |
| 57 | Caravan | Cover | Duke Ellington | 45 | 45 | Jan 20, 1990 | Dec 29, 1996 |
| 58 | A Life Beyond The Dream | Cover | Ghosts of the Forest | 43 | 43 | Jun 19, 2019 | May 2, 2026 |
| 59 | Bike | Cover | Pink Floyd | 43 | 42 | Nov 19, 1987 | Nov 2, 2018 |
| 60 | Memories | Cover | Van Alstyne and Kahn | 42 | 42 | Nov 17, 1990 | Jul 6, 1994 |
| 61 | If I Only Had a Brain | Cover | Ray Bolger (as âThe Scarecrowâ) | 41 | 41 | Mar 12, 1989 | Nov 16, 1995 |
| 62 | A Wave of Hope | Cover | Trey Anastasio | 40 | 40 | Aug 7, 2021 | Apr 30, 2026 |
| 63 | Quinn the Eskimo (The Mighty Quinn) | Cover | Bob Dylan | 39 | 39 | Apr 6, 1985 | Jun 28, 2019 |
| 64 | While My Guitar Gently Weeps | Cover | The Beatles | 38 | 38 | Oct 31, 1994 | Jul 19, 2025 |
| 65 | Drift While You're Sleeping | Cover | Ghosts of the Forest | 35 | 35 | Jun 11, 2019 | Apr 30, 2026 |
| 66 | Evolve | Cover | Trey Anastasio | 32 | 32 | Aug 4, 2021 | Apr 16, 2026 |
| 67 | Purple Rain | Cover | Prince | 32 | 32 | Jul 16, 1993 | Jul 4, 2012 |
| 68 | Corinna | Cover | Taj Mahal | 31 | 31 | Feb 21, 1987 | Oct 14, 2023 |
| 69 | I'm Blue, I'm Lonesome | Cover | Bill Monroe | 31 | 31 | Nov 16, 1994 | Jun 22, 2000 |
| 70 | Auld Lang Syne | Cover | Traditional | 30 | 29 | Dec 30, 1989 | Dec 31, 2025 |
| 71 | Free Bird | Cover | Lynyrd Skynyrd | 28 | 28 | Mar 6, 1987 | Nov 29, 2009 |
| 72 | Donna Lee | Cover | Charlie Parker | 28 | 28 | Oct 29, 1988 | Jul 25, 1993 |
| 73 | Lonely Trip | Cover | Trey Anastasio | 27 | 27 | Aug 11, 2021 | Apr 30, 2026 |
| 74 | The Star-Spangled Banner | Cover | Francis Scott Key | 27 | 27 | Oct 17, 1996 | Dec 28, 2016 |
| 75 | Oblivion | Cover | Trey Anastasio | 26 | 26 | Jul 11, 2023 | Apr 18, 2026 |
| 76 | Beneath a Sea of Stars Part 1 | Cover | Ghosts of the Forest | 24 | 24 | Jun 29, 2019 | Apr 17, 2026 |
| 77 | Daniel Saw the Stone | Cover | Traditional | 24 | 24 | Jul 15, 1993 | Jun 27, 2025 |
| 78 | Johnny B. Goode | Cover | Chuck Berry | 23 | 23 | Jun 17, 1995 | Jul 8, 1998 |
| 79 | Happy Birthday to You | Cover | Traditional | 23 | 22 | Dec 2, 1983 | Jul 23, 2023 |
| 80 | On Your Way Down | Cover | Allen Toussaint | 23 | 23 | Jun 24, 1988 | Jul 18, 2025 |
| 81 | Most Events Aren't Planned | Cover | Vida Blue | 23 | 23 | Aug 6, 2017 | Apr 17, 2026 |
| 82 | Life on Mars? | Cover | David Bowie | 23 | 23 | Oct 13, 1995 | Jun 29, 2012 |
| 83 | Izabella | Cover | Jimi Hendrix Experience | 22 | 22 | Jun 6, 1997 | Sep 20, 2025 |
| 84 | No Quarter | Cover | Led Zeppelin | 20 | 20 | Jun 1, 2011 | Jul 4, 2025 |
| 85 | Light Up Or Leave Me Alone | Cover | Traffic | 20 | 20 | Dec 6, 1986 | Jul 6, 2012 |
| 86 | Satin Doll | Cover | Duke Ellington | 20 | 20 | Jun 20, 1988 | May 8, 1993 |
| 87 | Hey Stranger | Cover | Trey Anastasio | 18 | 18 | Dec 29, 2022 | Apr 17, 2026 |
| 88 | Foreplay/Long Time | Cover | Boston | 17 | 17 | Oct 7, 1994 | Jul 12, 1999 |
| 89 | What's Going Through Your Mind | Cover | Trey Anastasio | 17 | 17 | Aug 7, 2024 | Apr 24, 2026 |
| 90 | Shaggy Dog | Cover | Sam Hopkins | 17 | 17 | Oct 15, 1986 | Oct 30, 2021 |
| 91 | Albuquerque | Cover | Neil Young | 17 | 17 | Jul 26, 1998 | Oct 13, 2023 |
| 92 | Have Mercy | Cover | The Mighty Diamonds | 17 | 17 | Apr 1, 1986 | Feb 22, 2020 |
| 93 | Ride Captain Ride | Cover | Blues Image | 17 | 17 | Mar 23, 1987 | Oct 26, 2013 |
| 94 | My Long Journey Home | Cover | Bill Monroe | 16 | 16 | Nov 16, 1994 | Nov 29, 1995 |
| 95 | Manteca | Cover | Dizzy Gillespie | 16 | 15 | Nov 4, 1990 | Feb 22, 2020 |
| 96 | Skin It Back | Cover | Little Feat | 15 | 15 | Oct 15, 1986 | Oct 21, 2018 |
| 97 | Soul Shakedown Party | Cover | Bob Marley and The Wailers | 14 | 14 | Feb 17, 1997 | Feb 1, 2025 |
| 98 | Sparks | Cover | The Who | 14 | 14 | Mar 23, 1987 | Dec 30, 2016 |
| 99 | Suspicious Minds | Cover | Elvis Presley | 13 | 13 | Sep 30, 1995 | Dec 6, 1996 |
| 100 | Strawberry Letter 23 | Cover | Shuggie Otis | 13 | 13 | Jul 22, 2017 | Jul 25, 2025 |