[2025] Smooth sailing at karaoke and work! Safe, fail-proof songs that won’t miss when singing karaoke with your boss or at business entertainment

Unlike karaoke with friends of a similar age or close coworkers, when it comes to karaoke as a second round after client dinners or drinks with bosses who are one or two generations older, you can’t help but be careful with your song choices.

Many new professionals are probably wondering what songs they should sing.

In this article, we introduce foolproof karaoke picks: timeless classics loved across generations—centered on the hit songs from your bosses’ youth—as well as recent buzzworthy tracks widely known even in mainstream households.

We’ve also selected Showa–Heisei era songs familiar to younger people via TikTok and more, so you’re sure to find something you can sing!