Lupe Fiasco Is The Jay Cutler Of Hip-Hop

Lupe Fiasco is the Jay Cutler of hip-hop. For those who may not know who Jay Cutler is, he is the polarizing NFL quarterback of the Chicago Bears. Since hip-hop and sports are my two favorite things to read and write about, I love making these kinds of comparisons. Sure, they don’t always hold up one-hundred percent, but they’re still fun to think about. Lupe Fiasco, like Jay Cutler, has enormous potential but he has never fully lived up to it.

Two Saviors of Chicago:

Both Cutler and Fiasco were seen as saviors early in their careers. Cutler was coming to a Chicago Bears franchise that hasn’t had a consistently good quarterback since the 1940s (shouts to Sid Luckman). Lupe Fiasco debuted in one of hip-hop’s worst eras – the ringtone rap/snap music era. The Bears gave up two first round draft picks in order to acquire Jay Cutler from the Denver Broncos. This put an enormous amount of pressure on the young quarterback, but he seemed to have all the makings of a franchise player – one of the strongest arms in the game, underrated mobility and the confidence of a superstar. Lupe also had a lot of pressure riding on his debut album, Food & Liquor. Mainstream hip-hop desperately needed a fresh, young voice; one whom could bring skill and technical proficiency to the masses.

Off to a Rocky Start:

Jay Cutler and Lupe Fiasco both had troublesome starts to their careers. Lupe Fiasco’s highly anticipated debut album leaked five months before the album was officially released. While the leaked version of the album received great reviews, this false start ultimately hurt the album’s sales because it got pushed back. Also several tracks on the original version of the album didn’t make the final cut, and many people believe the original leaked version of Food & Liquor is better than the official retail album.

Cutler’s career started out with a lot of instability. He had a break out season with the Denver Broncos in 2008, but after his head coach was fired, he was eventually traded to the Bears because the Broncos’ new coach did not get along with Cutler. Cutler had his worst season in his first year as a Bear, and many questioned if he was going to be a franchise quarterback.

Glimpses of Greatness:

Despite turmoil with the roll out of his first album, Lupe Fiasco flashed glimpses of his massive potential with his first two records. Both Food & Liquor and The Cool were uneven in certain parts, but were also among the best releases of 2006 and 2007. With songs like “Superstar” and “Kick, Push” Lupe Fiasco showed that he could bring great hip-hop to pop radio.

Cutler’s first season may have been disappointing, but in his second and third years with the Bears, he proved he could win games. In 2010 he went 10-5 (ten wins, five losses) as a starter and led the Bears to the NFC Championship Game, and in 2011 he went 7-3 and was playing some of his most efficient football of his career before breaking his thumb and missing the rest of the season.

Recent Disappointments:

What ultimately ties these two people is how they have been extremely disappointing in recent years. Despite all the good music Lupe Fiasco made on his first two albums, his recent projects have been increasingly frustrating. Lasers was a product of label politics. The album kept getting pushed back, and Lupe was forced to make pop records he didn’t want to do, including “Show Goes On,” which ironically is one of the few songs he raps well on. Food & Liquor II: The Great American Rap Album (Part 1) was supposed to be a return to his roots, but instead we got a bunch of pretentious, over-bloated raps over commercial productions. It was a mess.

Cutler’s 2014 season was full of turmoil. While his numbers were among the best he’s had as a Bear, the statistics didn’t show the whole story. Cutler’s yards per attempt was the second lowest of his career, and he was just completely uninspiring all season as the Bears finished with a 5-11 record. There was once a belief that with the right parts around him, he could be a winner. This season made me believe otherwise.

During the lowest parts of their respective careers, there were many similarities between Jay Cutler and Lupe Fiasco. For one, they both were extremely stubborn and aloof. Cutler is a bit notorious for never looking upset when things are going poorly. This leads to many wondering if he even cares if his team wins or loses (I think this is a dumb narrative made up by Chicago media and meatball fans). This sort of reminds me of Lupe Fiasco’s music over the past few years. Does Lupe even care about making good songs or does he just want to fight his label and push his political agendas?

Ultimately both of these guys seem to completely shut down when things don’t go their way. When things are going bad for Cutler and the Bears, Jay rarely rises above and makes his team better. He usually stoops down to the level of play like the rest of his team, and he ends up making poor decisions with the football. This happened nearly every game in the 2014 season, and it’s my main criticism of Cutler. One of my favorite Bears blogs, “Start Kyle Orton” describes this trend as “Fuck It Jay.”

Lupe Fiasco also has a “Fuck It Fiasco” persona. Time and time again he’s plotted his exit from hip-hop music. He planned on retiring after his third album due to troubles with his label – ergo, Lupe shuts down when things don’t go his way. When Atlantic Records shelved his third album, he shut down. Instead of playing along and trying to make good pop songs (like he did with “Superstar,” “Hip Hop Saved My Life,” and “I Gotcha”), he mailed in lazy verses all over Lasers.

The Chicago Renaissance:

I wrote about ninety percent of this piece before I heard Lupe’s newest album, Tetsuo & Youth. Admittedly, I wrote this fully expecting Lupe’s fifth album to totally suck. But it didn’t suck (as per my review). It was a great record, and saying it is his best since The Cool is a total understatement.

Now this sort of spoils my narrative comparing Lupe Fiasco’s career to Jay Cutler’s time with the Bears. Lupe Fiasco made some of the best music of his career when most people had given up on him. It seemed like his career was over, and I figured his best days were well behind him. Now with Tetsuo & Youth, Lupe is experiencing a bit of a career renaissance.

It was a total train wreck of an ending to Jay Cutler’s 2014 season with the Bears. But with a new coaching staff coming into Chicago, it seems like Jay might get one more chance. Just about the entire city of Chicago (and most football fans in general) has given up him. I thought I would be retiring my number 6 jersey after the Bears’ 13-9 loss to the Vikings – a game I depressingly watched at a bar in Toledo, Ohio waiting for my Greyhound bus to take me back to Chicago. A little less than a month later another former savior of Chicago, Lupe Fiasco, made me a believer again with his new album. Hell, if Lupe can turn things around, why can’t Jay Cutler?

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The author Goose

Goose is a talented writer who loves hip hop and writes for RapReviews and Okayplayer. Goose brings a fresh, new dimension to The Hip Hop Speakeasy and loves any opportunity he has to share the love of hip-hop that he knows so many people have.