Songfacts®:

• One of the most joyful songs ever recorded, "Send Me On My Way" was never a huge hit, but roughly a decade after it was released, it found its way to various media uses to convey a pleasant journey. It was featured in the movies Matilda and Ice Age, on the TV shows Chuck and New Girl, and in ubiquitous commercials for Enterprise Rent-A-Car, which built an ad campaign around the song.
  
  Rusted Root had seven members at the time, and they all shared the songwriting credit on this one. Their frontman Michael Glabicki wrote the lyrics, and their other members - Liz Berlin, John Buynak, Jim Dispirito, Jim Donovan, Patrick Norman and Jennifer Wertz - contributed to the track. Glabicki told us about writing the song: "I remember just walking right into our studio during the day. I remember it being very sunny. We had these big windows in this warehouse and the sun was shining in, and as soon as I walked in I picked up the guitar and just started writing it. It was just a very, very happy feeling. You could feel that there was a lot of happiness in the room. Whether that was an extension of me or something else in there that was very happy, you just felt it. Just like a super happy feeling." (Here's our full interview with Michael Glabicki.)
• This song contains the most famous penny whistle solo since Morris Goldberg used one on Paul Simon's "You Can Call Me Al." It was played by Rusted Root band member John Buynak (Johnny B.). Michael Glabicki told us how it happened: "When I first went to hang out with him and played some music, it was kind of like visiting the Hobbit. He had all these little toys laying around and he would just randomly bop around and pick up different little things, whether it was a flute or a saxophone or penny whistles or little percussion things that he had all laying out in his apartment. I don't think he considered himself a musician at the time, but he just had this great light energy to him.
  
  When I asked him to join, it was mainly for the flutes and the woodwinds. He was like a little wizard guy, he picked up these things and just played around with them. And the first time he heard the song, it was kind of goofy. Everybody was happy - there was this happy vibe over the room. Jenn (Wertz) was going, 'On my way, on my way,' real goofy like. And Johnny picked up the penny whistle and they were doing this little goofy dance and just having fun and laughing with it. That's how the penny whistle part came about."
• There are some phrases in this song that if you believe hard enough can form real words, but are really just made up. One part sounds like "Oohmaseeyou," and another like "Mamasaydobeddyalong." Michael Glabicki says that these words aren't supposed to make rational sense. He explained: "I was in the process of coming up with lyrics, and it just sounded so good and felt so right that it had a meaning of its own that you couldn't make better by making it a word. So I left it."
• An influence on this song was Toni Childs, an American singer who uses many African sounds in her work. Like Rusted Root, she had just one Hot 100 entry ("Don't Walk Away," 1988) and it also placed at #72.
• Cruel Sun was Rusted Root's 1992 debut album, and contained the first version of this song. Two years later, a new version was included on their second album When I Woke, which was the charting single (It didn't hit the charts until a year after the album was released). It did very well with the college crowd, and for a while it looked like the band would follow the trajectory of Blues Traveler and Dave Matthews Band, but "Send Me On My Way" never got the exposure of "What Would You Say" or "Run-Around," and they never became headliners or radio stars.
  
  Regarding the song's success, Michael Glabicki told us: "It made it onto a good portion of radio stations across the United States. And I think where it really came about was on college campuses. It was spread by word of mouth and just by college students. I think that's how the song really had its foundation. But we did get some pretty significant radio play, so there was that portion of it, too. I think it wasn't more a matter of being marketed a certain way, it was more the industry and how the industry was on the brink of changing drastically at that point."
• The original version on Cruel Sun runs 4:57. The 1994 When I Woke version was cut to 4:19, and edited down to 3:56 for the single. Bill Bottrell, who was Sheryl Crow's collaborator on her debut album Tuesday Night Music Club, produced When I Woke, including the updated version of "Send Me On My Way."