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In 2008, the duo went to the Ardent studios in Memphis, Tennessee to record their sixth album, Back When I Knew It All.

Once again, they worked with Blake Chancey as producer.

This album's title track, co-written by Trent Willmon, was the duo's fastest-climbing single.

Both it and followup " Roll with Me ", which included a backing vocal from Five for Fighting, went to number 1.

" One in Every Crowd ", co-written by Montgomery with Kim Tribble and former Trick Pony bassist Ira Dean, was issued in January 2009 as the third single.

By the middle of the year, this song peaked at number 5.

The fourth single, the number 23 " Long Line of Losers ", was co-written and previously recorded by Kevin Fowler.

Toby Keith, with whom Montgomery Gentry toured in mid-2008, contributed a guest vocal on the Terri Clark co-write " I Pick My Parties ", and Lillie Mae Rische of Jypsi made an appearance on " God Knows Who I Am ".

Thom Jurek wrote of this album, " The hardcore fans will love it, but this isn't the album that will win over many new ones.