- Lester Flatt — Lead Vocals, Guitar
- Bill Monroe — Tenor Vocals, Mandolin
- Earl Scruggs — Banjo
- Robert Russell "Chubby" Wise — Fiddle
- Howard "Cedric Rainwater" Watts — Bass
“The Old Crossroads” is a warning sung to a brother: don’t let Satan take your hand, or you will be lost in sin and never reach the promised land. The crossroads is waiting, and the singer asks which way the listener will go, since one road leads down to destruction and the other up to the pearly gates, with Jesus to guide the traveller at the fork. Life will soon be over, the last verse says, and everyone will have to face that choice.
Bill and Charlie Monroe recorded it as the Monroe Brothers in Charlotte, North Carolina, on 12 October 1936, Charlie singing lead and playing guitar, Bill singing tenor on mandolin. Bluebird issued “The Old Crossroad” that December (B-6676), backed with “We Read of a Place That’s Called Heaven.” Bill Monroe recorded it again with the Blue Grass Boys at the WBBM studios in Chicago on 27 October 1947: Lester Flatt sang lead and Monroe tenor, with Monroe on mandolin, Flatt on guitar, Earl Scruggs on banjo, Chubby Wise on fiddle and Howard Watts (“Cedric Rainwater”) on bass. Columbia released it in May 1949 as “Old Cross Road” (20576), credited to Bill Monroe, with “Remember the Cross” on the other side. Nearly forty years later Monroe cut it once more, on 19 August 1986 in Nashville for the MCA album Bluegrass ’87, with Tom Ewing singing lead, Monroe tenor, Blake Williams baritone and Clarence “Tater” Tate bass.
Sonny Osborne recorded it at the Gateway studio in Cincinnati in October 1952 for the Kentucky label (565). Rose Maddox sang it as “The Old Crossroads Is Waitin’” on her 1962 Capitol LP Rose Maddox Sings Bluegrass, recorded on 19 March 1962 with Don Reno on banjo, Red Smiley on guitar and Donna Stoneman on mandolin. Ralph and Carter Stanley recorded it in Baltimore in December 1963, with George Shuffler singing lead and Ralph Stanley tenor; one take appeared on the Wango LP John’s Gospel Quartet (1966), issued under that name. Ricky Skaggs and Tony Rice sang it as a duet, with only guitar and mandolin, on Skaggs & Rice (Sugar Hill SH 3711, 1980); that LP credits the song to Charlie Monroe.