October 25, 1999: "A Few Old Memories" is released as the first single from Dolly's thirty-seventh solo studio album, The Grass Is Blue.
October 25, 2018: Buck Trent released his Spartanburg Blues album. Dolly is the featured vocalist on a new recording of "The Carroll County Accident", which she had previously recorded for her 1969 album, In the Good Old Days (When Times Were Bad).
October 25, 2019: Galantis and Dolly release the dance single, "Faith", featuring Mr. Probs. The single peaked at number 29 on the Billboard Dance Club Songs chart.
October 26, 1999: Dolly released her thirty-seventh solo studio album, The Grass Is Blue. It peaked at number 24 on the Billboard Top Country Albums chart. The album won Album of the Year at the 2000 International Bluegrass Awards. It won Best Bluegrass Album at the 43rd Annual Grammy Awards in 2001, while the album track "Travelin' Prayer" received a nomination for Best Female Country Vocal Performance.
October 26, 2009: Kenny Rogers released The First 50 Years box set. The set features a new duet by Kenny and Dolly titled "Tell Me That You Love Me".
October 27, 1997: "Something Bigger Than Me" is released as a single from the Annabelle's Wish soundtrack album.
October 27, 2009: The 4-disc, career-spanning boxset, Dolly, is released. The set includes seven previously unreleased tracks and peaked at number 59 on the Billboard Top Country Albums chart.
October 27, 2021: Dolly's duet with Jimmy Fallon, "All I Want for Christmas Is You", is re-issued as a single to Hot/Modern/AC radio formats. It had previously been issued to country stations in 2020.
October 28, 2008: The Born to the Breed: A Tribute to Judy Collins compilation album is released. Dolly contributed "Fisherman's Song" to the album.
October 28, 2011: "He’s Everything" by Queen Latifah, Dolly, Keke Palmer, Jeremy Jordan, Andy Karl, and DeQuina Moore is issued as the first single from the Joyful Noise soundtrack album.
October 29, 1984: Kenny Rogers and Dolly released their Once Upon a Christmas album. It peaked at number 12 on the Billboard Top Country Albums chart and went on to be certified 2x Platinum by the RIAA for shipment of 2,000,000 copies.
Image credit: misteredd at discogs.com
October 29, 1984: Gail Davies released her Where Is a Woman to Go album. Dolly provides harmony vocals on a cover of "Unwed Fathers", which was written by John Prine and Bobby Braddock, and first recorded by Tammy Wynette in 1983. The album peaked at number 57 on the Billboard Top Country Albums chart.
October 29, 2002: Patty Loveless released her Bluegrass & White Snow: A Mountain Christmas album. Dolly and Ricky Skaggs provide backing vocals on the title track, "Bluegrass, White Snow". The album peaked at number 20 on the Billboard Top Country Albums chart.
October 20, 1967: Porter Wagoner and Dolly's first duet single, "The Last Thing on My Mind", is released. It peaked at number seven the Billboard Hot Country Songs chart.