As this week's celebrity mentor, Connick schooled the top five contestants on the music of Frank Sinatra. He arranged all the song choices, wrote the orchestrations, and even sat in on the piano accompanying each contestant.
His moral support helped elevate painter Lee DeWyze to a new competitive level. The two got along exceptionally well during their practice session, which gave DeWyze the confidence boost he needed to shine.
"He looks like a new and improved version of me," said Connick, after noting that his wife is a big fan of the young singer.
DeWyze's rendition of "That's Life" received the highest praise from the judges. Simon Cowell dubbed his rock-style performance the best of the night, while Ellen Degeneres said he would have won the whole competition if this was his last.
Michael "Big Mike" Lynche also impressed the judges with his version of "The Way You Look Tonight." Sporting a fedora and a striped vest, Lynche looked comfortable and played the stage well. He kept his staple R&B style and delivered a performance that pleased the judges.
"You're in it to win it!" Randy raved, and everyone else agreed.
Aaron Kelly started off the night by singing "Fly Me To The Moon," which booth Randy and Ellen deemed a solid performance. Kara was more critical and thought the 17-year-old could have used a little more charisma to fill the stage more, but she reassured him, reminding the young singer he'd be back next week.
Casey James tried to hold his own without his guitar but fell short. His performance of "Blue Skies" came out too forced and just didn't work for any of the judges, which was a shame since it seemed like Connick was really pushing for him to do well.
For the second week in a row, Crystal Bowersox failed to impress the judges. Although she looked chic and quite glamourous in her black, strapless gown, Bowersox was out of her element and provided a sleepy and subdued performance. Simon said it felt a little indulgent and he expected better.
Now that DeWyze and Lynche are on top, Kelly, James and Bowersox will most likely face the dread of elimination on Wednesday when the top five are hacked down to a new top four.