Before that, he tallied six Hot 100 entries in the '90s, reaching a No. 18 decade-high with "Forever in Love" in 1993, and charted his first four in the '80s, including his debut hit, the No. 4-peaking "Songbird."
Kenny G's decade-by-decade totals: three top 40 Hot 100 hits in the '80s, two in the '90s and one each in the '00s and '10s. Notably, timing was on his side just enough, as he appeared on the chart in the first month of the '00s and now returns with just over a month left in the '10s.
Kenny G is the first act to have notched top 40 Hot 100 titles in each of the past four decades since U2, which also joined the club thanks to a featured turn on a rap hit: Kendrick Lamar's "XXX.," featuring the band, debuted at its No. 33 peak in May 2017. U2's lone top 40 hit this decade followed six in the '80s, seven in the '90s and three in the '00s.
Jackson's decade-by-decade breakdown of sending new songs into the Hot 100's top 40: 18 in the '80s, 10 in the '90s, two in the '00s and three in the '10s, most recently as featured on Drake's "Don't Matter to Me," which bowed and peaked at No. 9 in July 2018. (That's on top of Jackson's seven top 40 hits as a soloist in the '70s; the late King of Pop is also the only act with top 10 Hot 100 hits in each of five decades.)
From the King of Pop to the Queen, Madonna most recently reached the Hot 100's top 40 in 2012 with the No. 10-peaking "Give Me All Your Luvin'," featuring Nicki Minaj and M.I.A. Madonna by the decades: 19 top 40 hits in the '80s, 20 in the '90s, nine in the '00s and one in the '10s.
Meanwhile, pop parody icon Yankovic boasts four top 40 Hot 100 hits, having spaced out one spoof per decade, extending his run through the '10s with "Word Crimes" (No. 39, 2014), which sends up Robin Thicke's 12-week 2013 No. 1 "Blurred Lines," featuring T.I. and Pharrell.
(Note that this research excludes both Bon Jovi and Whitney Houston, who charted top 40 hits in the '80s, '90s, '00s and '10s, but only in the current decade via re-entries of prior hits.)
Ultimately, Kenny G, Jackson, Madonna, U2 and Yankovic have all managed to stretch their runs of top 40 Hot 100 hits to historic levels by adapting, thanks to assists from acts who've followed them onto the charts, including Lamar, Drake, Minaj, Thicke and, as of this week, Kanye West.