Billy Gunn

Context: After The Smoking Gunns disbanded, Gunn took some time off to nurse an injury. At WrestleMania 13, he defeated Flash Funk catching the attention of The Honky Tonk Man, who made Gunn his protege. During this time, he adopted a new gimmick, Rockabilly, and had a short-lived feud with "The Real Double J" Jesse James. On Shotgun Saturday Night, James realized both of their careers were going nowhere and suggested that they became a tag team. Gunn agreed and smashed a guitar over the Honky Tonk Man's head to solidify their new alliance.  James and Rockabilly were quickly rebranded as "Road Dogg" Jesse James and "Badd Ass" Billy Gunn, respectively, and their tag team formed was soon dubbed the New Age Outlaws. This new team was in the spirit of the new Attitude Era: brash, vulgar, egotistical, and loud-mouthed. They quickly rose to the top of the tag team ranks and won the Tag Team Championship from the Legion of Doom on November 24. They also defeated the LOD in a rematch at In Your House: D-Generation X.  The Outlaws slowly began to align themselves with D-Generation X, who were impressed with their new attitude. At the Royal Rumble, the New Age Outlaws interfered in a Casket match to help Shawn Michaels defeat The Undertaker. At No Way Out Of Texas, the Outlaws teamed up with Triple H and Savio Vega (who replaced the injured Shawn Michaels) to face Chainsaw Charlie, Cactus Jack, Owen Hart, and Steve Austin. They were, however, defeated. On February 2, The Outlaws locked Cactus and Chainsaw in a dumpster and pushed it off the stage. This led to a Dumpster match at WrestleMania XIV where Cactus and Chainsaw defeated the Outlaws for the Tag Titles. The next night on Raw, the New Age Outlaws won the Tag Team Championship for a second time by defeating Chainsaw and Cactus in a Steel cage match, but only after interference from Triple H, Chyna, and X-Pac. After the match, the Outlaws officially became members of D-Generation X (DX). Upon becoming an official member of DX, Gunn gained a tendency of mooning opponents (a trait used by the original incarnation of DX, as well as its 2006 revival), a precursor to the later "Mr. Ass" gimmick.  After joining DX, the Outlaws successfully defended their Tag Team Title against the Legion of Doom 2000 at Unforgiven. DX began to feud with Owen Hart, and his new stablemates, The Nation. At Over The Edge, the Outlaws and Triple H were defeated by Nation members Owen, Kama Mustafa, and D'Lo Brown in a Six Man Tag Match. The Outlaws would also successfully defend their title against The New Midnight Express (Bombastic Bob and Bodacious Bart) at King of the Ring.  During this time, the Outlaws began a feud with Kane and Mankind. Although Kane and Mankind won the Tag Team Championship, they could not get along. At SummerSlam, Mankind faced the Outlaws in a Handicap match after Kane no-showed the title defense. The Outlaws defeated Mankind to win the titles for the third time. The Outlaws then helped X-Pac in his feud with Jeff Jarrett and Southern Justice. In December, the Outlaws lost the title to The Big Boss Man and Ken Shamrock from The Corporation. CANNOTANSWER

Question: Did Jesse James and Billy Gunn ever lose?
Answer: teamed up with Triple H and Savio Vega (who replaced the injured Shawn Michaels) to face Chainsaw Charlie, Cactus Jack, Owen Hart, and Steve Austin. They were, however, defeated.