While the Bosstones weren't the most successful of the 'Third Wave' ska bands--arguments can be made for both No Doubt and 311 having that distinction--the Bosstones were certainly amongst the top ten acts from that revival, thanks mainly to the surprise popularity of "The Impression That I Get" from Let's Face It. The strength of that single allowed Dickey Betts and company to keep going for a live collection and two more studio albums, the last of which, From A Jacknife To A Swain, spawned today's song.
I think the biggest impediment to the band's popularity is also its greatest strength, namely the vocals of Dicky Betts. By no means a polished, professional singer when the Bosstones started out, Betts still had a raw emotionality that propelled their songs, making them into more than they maybe should have been. Oddly enough, one of the reason Jacknife may have been something of a flop is because Dicky seemed to have gotten some singing lessons and become more pleasing to the ear....but at the expense of that emotionality.
The song itself is a little fluffy (which might also explain why the album tanked; there are a number of lighter songs like this which both blunts the impact of the overall album while also making the more 'traditional' Bosstones songs like "Mr. Moran" and "I Want My City Back" sound uglier by comparison), but it's pleasant enough for what it is.