Question: "These Are the Times" is the second single released from the second album of Dru Hill, an American singing group, most popular when?

Context paragraphs:
Return of Dragon: Return of Dragon is the second studio album by American R&B recording artist Sisqó of Dru Hill, released on June 19, 2001 on Def Soul Records.  The album did very well on the charts but its singles, "Can I Live" and "Dance for Me", were commercial disappointments compared to his debut album, "Unleash the Dragon" (1999).  Despite the fact that Sisqó announced a third single, "Dream", this never materialized due to the commercial failure of the album.  The song "Without You" was originally planned to be featured on Dru Hill's third album, "Dru World Order" but tensions grew between the group while working on the album and it was put on hold.  "Return of Dragon" was later certified Platinum by the Recording Industry Association of America (RIAA) for excess of one million copies.  "Return of Dragon" would be Sisqó's last album until "Last Dragon" (2015).

In My Bed: "In My Bed" is a number-one platinum-selling R&B single by R&B group Dru Hill.  It is the second single from their eponymous debut album.  The single spent three weeks at number-one on the US R&B chart and peaked at number four on the US pop chart.  The song is performed by group leader Mark "Sisqó" Andrews.  The music video focuses on Sisqó's girlfriend, who cheats on him with another man and the other members of the group, but Sisqó doesn't know anything about it.  At the end of the video, Sisqó goes to his house with a bouquet of flowers for his girlfriend when he sees a guy walking out.  He goes inside and sadly finds her in bed with a woman and drops the flowers in heartbreak.  He leaves the house for a few seconds and goes back in.  The remix features Jermaine Dupri, who also produced the track, and Da Brat.  It was a hit single.  The remix sampled Le Pamplemousse's "Gimme What You Got" (1976).

These Are the Times: "These Are the Times" is the second single released from Dru Hill's second album, "Enter the Dru".  The single reached number 21 on the Hot 100 and number 5 on the R&B chart, staying on the chart for 21 weeks.  The music video directed by Bille Woodruff was inspired by the film "The Man in the Iron Mask".  Sisqó played both the good twin and the evil twin and Jazz, Woody and Nokio played the Musketeers.  Actress Lark Voorhies appears in the video as Sisqó's love interest.

Dru World Order: Dru World Order is the third studio album by American R&B group Dru Hill, released in late 2002 (see 2002 in music) on Def Jam Recordings' Def Soul imprint.  Four years had passed between this release and the group's previous album, "Enter the Dru", during which time the quartet imploded, yet later reformed.  Beginning with this release, Dru Hill became a quintet, with fifth member Scola (Rufus Waller) added to the original lineup of Sisqó, Jazz, Nokio, and Woody.  This was the first and only time that Dru Hill was featured as five members.  The album released three singles "I Should Be...", "I Love You" and "No Doubt".  Two of the singles had music videos released.  This is the group's last album for the entire Def Jam roster and they were released from their contract within a year due to poor album sales for this album and Sisqó's second album, which caused the group to go on a second hiatus.

Enter the Dru: Enter the Dru is the second studio album from American R&B group Dru Hill, released October 27, 1998 on Island Records.  The album's name comes from Bruce Lee's film, "Enter the Dragon".  This is the first album that the group were credited as executive producers as all four members wrote and produced several of the songs.  It released three singles "How Deep Is Your Love", "These Are the Times" and "You Are Everything".  The singles all had music videos released, but the music video for "You Are Everything" was a remix video, which featured rapper Ja Rule, and Woody did not appear in it due to his exit from the group in early 1999.  The remix version was featured on lead singer Sisqó's debut album, "Unleash the Dragon".  Recording sessions for the album took place at Larabee Studios in Los Angeles, California.  The album peaked at number two on the "Billboard" 200 chart.  On May 1999, It was certified double-platinum in sales by the Recording Industry Association of America (RIAA), after sales exceeding 2,000,000 copies in the United States.

Dru Hill: Dru Hill is an American singing group, most popular during the late 1990s, whose repertoire included soul, hip hop soul and gospel music.  Founded in Baltimore, Maryland, and active since 1992, Dru Hill recorded seven Top 40 hits, and is best known for the R&B #1 hits "In My Bed", "Never Make a Promise", and "How Deep Is Your Love".  The group consist of lead singer Mark "Sisqó" Andrews (who went on to have a very successful solo career), Tamir "Nokio" Ruffin and, Larry "Jazz" Anthony, and James "Woody Rock" Green.

InDRUpendence Day: InDRUpendence Day is the fourth studio album by American R&B group Dru Hill, released on July 27, 2010 under Kedar Entertainment Group.  The album was supposed to be released on June 8, 2010, but it was pushed back.  The album is the group's first release with new member, Tao, and is also their first album in eight years since their previous album, "Dru World Order".  The album released three singles: "Love MD", "Remain Silent" and "Back to the Future".  "Love MD" is the only single that had a music video released.  Despite the lack of charting singles and the fact that it was their first album in 8 years, the album was still moderately successful, reaching #30 on the Billboard 200.

Dru Hill (album): Dru Hill is the self-titled debut studio album from American R&B group Dru Hill, released November 19, 1996 on Island Records.  The album featured four singles "Tell Me", "In My Bed", "Never Make a Promise" and "5 Steps".  All of the singles had music videos released.  The album also features the So So Def remix of "In My Bed", which features Jermaine Dupri and Da Brat, as a bonus track, which also had a music video released.

How Deep Is Your Love (Dru Hill song): "How Deep Is Your Love" is an R&B single by group Dru Hill and features rapper Redman.  It is the first single from the group's second album, "Enter the Dru".  The song was released on September 22, 1998, the hit song spent three weeks at number-one on the US R&B chart, and peaked at number-three on the US Pop chart.  The song was also used in the end credits and is featured on the soundtrack to the 1998 film "Rush Hour".  The music video directed by Brett Ratner was shot on top of Hopewell Centre in Wan Chai, Hong Kong and features clips from "Rush Hour".  Redman's verse is cut from both the group's album and the video version as he does not appear in the video.This song was also one of the hottest songs for club mix music that originated out of their hometown on Baltimore.

Phoenix Rising (The Temptations album): Phoenix Rising is a 1998 album by The Temptations for the Motown label, featuring the debut of new Temptations Barrington "Bo" Henderson, Terry Weeks, and Harry McGilberry.  The album, the Temptation's first million-selling album in twenty years, features the hit single "Stay", which samples the group's 1965 hit "My Girl".  Although not commercially released as a single, "Stay" was a Top 30 R&B Hit, peaking at #26, and it became a #1 hit on the Adult Contemporary Charts.  The Temptations' "Phoenix Rising" was certified Platinum by the RIAA November 15, 1999.  The album is having the same fate as Dru Hill's "Enter the Dru", and 112's "Room 112".

Supporting paragraphs: These Are the Times Dru Hill
Answer: late 1990s