[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!
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[2025] Smooth sailing at karaoke and work! Safe, crowd-pleasing songs that won’t miss with your boss or at business karaoke (1–10)
HOWEVERGLAY
Speaking of GLAY’s songs, they span from energetic numbers to moving ballads, and many are easy to sing at karaoke—so it can be tough to choose.
If you want to share a touching moment across generations at a work karaoke with your boss, their signature ballad released in August 1997 is a great pick.
This majestic, stirring track conveys unwavering devotion to a loved one and a strong determination for the two to overcome any hardship together.
TERU’s emotive vocals further elevate the tender yet warm message.
It topped the Oricon charts, sold over a million copies, and was later used as the ending theme for a TBS drama, so many people are sure to recognize it.
As a timeless love song cherished across generations, it’s sure to create a warm atmosphere.
One Night CarnivalKishidan
It can be considered one of Kishidan’s signature songs, singing of carnival-like excitement and a sense of liberation.
The lyrics, which depict the sparkle of youth and the yearning to be free from constraints, resonate across generations.
Released as a single on May 29, 2002, under the EMI label, it has since seen numerous collaborations with various artists.
In 2013, a remake was also released as the theme song for “Kishidan Banpaku 2013.” It’s an ideal choice for karaoke with bosses or at business entertainment settings, as it can liven up the room regardless of age.
With a melody everyone knows and lyrics that are easy to sing along to, it’s sure to instantly elevate the atmosphere.
cherry (cherry fruit; sakuranbo)Ai Otsuka
Among Ai Otsuka’s works, this is truly a timeless classic that brightens listeners’ hearts and is loved across generations.
The lyrics, which look back on precious moments spent with a lover while singing of hope for the future, overflow with a universal appeal that resonates with anyone.
The expression that likens two fruits nestled close together to the couple’s relationship is also wonderfully cute and memorable.
This piece was released in December 2003 as her second single and is included on the album “LOVE PUNCH.” Many will recognize it as the opening theme for TBS’s music program “COUNT DOWN TV” and the ending theme for Fuji TV’s variety show “Mecha-Mecha Iketeru!” Even in slightly tense situations like karaoke with your boss, the song’s happy vibe will help lighten the mood.
[2025] Smooth Sailing at Karaoke and Work! Safe Song Choices That Won’t Miss with Your Boss or Client Karaoke (11–20)
catDISH//
This song, which portrays the ache of unrequited love and the pain of parting, is a classic that resonates with younger generations.
The protagonist’s wish for the person they lost to return like a cat is delicately expressed, striking a deep chord with listeners.
Released in August 2017, it has continued to be loved by many as one of DISH//’s signature songs.
The acoustic version on THE FIRST TAKE also garnered attention, and it became a massive hit with over 500 million streams.
With its warm vocals and melody that appeal to a wide range of ages, it’s a track that eases the atmosphere—even at karaoke with your boss or at business functions.
Bling-Bang-Bang-BornCreepy Nuts
When it comes to the song that dominated Japan’s music scene in 2024, Creepy Nuts’ “Bling-Bang-Bang-Born” is the obvious pick.
Released in January 2024 as the opening theme for the second season of the TV anime “Mashle: MAGIC AND MUSCLES,” it skyrocketed in popularity, with the opening video surpassing 10 million views just two weeks after its release—hard to forget that level of hype.
Its spell-like, instantly catchy phrases and the dance everyone copied on social media propelled it up the charts both in Japan and abroad.
The lyrics overlap the image of a protagonist carving a path with extraordinary power and the duo’s own hip-hop dream, creating an irresistible pull for listeners.
If you want a karaoke track that brings people together across generations, this one is a must.
Water lily flowerShonan no Kaze
An energetic track quintessentially Shonan no Kaze—one that instantly sweeps listeners into the heat of summer—arrived in June 2007 as their sixth single, leaving a vivid mark on the music scene by reaching No.
2 on the Oricon weekly chart.
It unfolds from an intro steeped in traditional Japanese sentiment into an uptempo rhythm that boldly incorporates soca from the Caribbean, and the familiar towel-spinning has become a live-show staple.
The lyrics are not merely cheerful; they center on the strength and vitality to overcome hardship and grasp hope.
According to member Wakadanna, the song embodies an attitude of “living.” In 2008, this summer anthem won Best Reggae Music Video at the MTV Video Music Awards Japan, and because it fires up audiences across generations, it’s perfect for building a sense of unity when singing karaoke with your boss and colleagues.
Beat de TouhiHamaiku
It’s a song filled with positive energy that blows away everyday little frustrations and boredom with a pleasant rhythm.
The lyrics, infused with songwriter meiyo’s belief that “music is an escape,” gently resonate with listeners and invite empathy.
The harmony woven by the distinctive duo—Ryuichi Hamaya from Kamaitachi and Erika Ikuta—is also captivating.
Released in November 2022, this piece is the debut track of a unit born from NHK’s music program Venue101, and they also appeared in a special segment of that year’s Kōhaku Uta Gassen, drawing attention from viewers at home.
Its up-tempo, catchy melody is sure to liven the mood even at karaoke with your boss, and if you add the simple, TikTok-familiar choreography, it’s guaranteed to be fun across generations.